5H-furan-2-one derivatives stabilization of organic material

ABSTRACT

A composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation; and b) a compound of formula I (Formula I) (I) where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9  and R 10  are independently from each other H, C 1 -C 8 -alkyl, C 4 -C 8 -cycloalkyl, phenyl, C 1 -C 4 -alkoxy or halogen; n is 1, 2, 3, or 4; and when n is 1 A is —C(=0)-OR′ 1 , —C(=0)-N(R ′2 )(R′ 3 ), —CN, phenyl, which is unsubstituted or substituted by one or more C 1 -C 8 -alkyl, C 4 -C 8 -alkoxy, C 5 -C 7 -cycloalkyl or halogen, —H or —S0 2 -phenyl; when n is 2 A is —C(=0)-0-Z 1 —O—C(=0)-, —C(=0)-N(R″ 1 )—Z 2 —N(R″ 2 )—C(=0)- or piperazine-N,N′-biscarbonyl.

CROSS-REFERENCE TO RELATED APPLICATIONS

This is a continuation of U.S. patent application Ser. No. 14/114,538, filed Oct. 29, 2013, which is the U.S. national phase of International Patent Application No. PCT/IB2014/052064, filed Apr. 25, 2012, which claims the benefit of European Patent Application No. 11164465.4, filed May 2, 2011 and U.S. Provisional Patent Application No. 61/481,272, filed May 2, 2011, each incorporated herein by reference in its entirety.

DESCRIPTION

Organic materials are susceptible to degradation, which can be induced by heat, light and/or oxidation. For reducing such degradation, numerous solutions in regard to an incorporation or addition of a stabilizer are proposed.

There is still a need for further technical solutions towards stabilisation of organic material against the detrimental impact of heat, light and/or oxidation.

US-A-2003/0083405 discloses inter alia 5H-dihydro-furan-2-one derivatives as antioxidants for stabilization of a polymer.

It has now been found that a specific group of 5H-dihydro-furan-2-one derivatives are suitable for stabilization of organic material against degradation by heat, light and/or oxidation.

The present invention relates to a composition, which comprises

-   a) an organic material susceptible to oxidative, thermal or     light-induced degradation; and -   b) a compound of formula I

wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is     unsubstituted or substituted by one or more C₁-C₈-alkyl,     C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen, —H or —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or     piperazine-N,N′-biscarbonyl; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl),     3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl),     1,4,7-triazaheptane-1,4,7-tricarbonyl,     1,4,8-triazaoctane-1,4,8-tricarbonyl or     1,5,9-triazanonane-1,5,9-tricarbonyl; -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl),     1,4,7,10-tetraazadecane-1,4,7,10-tetracarbonyl,     1,4,8,11-tetraazaundecane-1,4,8,11-tetracarbonyl or     1,5,8,12-tetraazadodecane-1,5,8,12-tetracarbonyl; -   n is 1, 2, 3 or 4; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,     C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to     three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or     tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which     is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which     is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is     interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,     which is substituted by a hydroxyl group, C₆-C₁₀-aryl,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     5-, 6- or 7-membered saturated heterocycle; -   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,     C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms,     hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or     1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and -   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,     C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms,     3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

A compound of formula I possess at least one asymmetric carbon atom, i.e. the carbon atom at the 5-position of the furan-2-one ring, which results in enantiomers. The invention relates to any one of these enantiomers or mixtures therof. Several combinations of substituents at formula I lead to the presence of at least two asymmetric carbon atoms, which results in diastereomers. The invention relates to any one of these diastereomers or mixtures thereof.

C₁-C₂₂-alkyl is linear or branched and for example methyl, ethyl, n-propyl, 1-methyl-ethyl, n-butyl, 1-methyl-propyl, 2-methyl-propyl, 1,1-dimethyl-ethyl, n-pentyl, 1-methyl-butyl, 3-methyl-butyl, n-hexyl, 1-methyl-pentyl, 2-methyl-pentyl, 4-methyl-pentyl, 2-ethyl-butyl, n-heptyl, 1-methyl-hexyl, n-octyl, 1-methyl-heptyl, 2-ethyl-hexyl, 5,5-dimethyl-hexyl, 1,1,3,3-tetramethyl-butyl, n-nonyl, 2-ethyl-heptyl, n-decyl, undecyl, n-dodecyl, tridecyl, tetradecyl, pentadecyl, n-hexadecyl or n-octadecyl. Preferred is C₁-C₁₈-alkyl, in particular C₁-C₁₂-alkyl, especially C₁-C₈-alkyl, very especially C₁-C₄-alkyl.

C₂-C₁₈-alkenyl is linear or branched and for example vinyl, allyl, Z- or E-but-2-ene-yl, Z- or E-but-3-ene-yl, Z- or E-pent-2-ene-yl, pent-4-ene-yl, Z- or E-2-methyl-but-2-ene-yl, Z- or E-3-methyl-but-3-ene-yl, Z- or E-hex-1-ene-yl, Z- or E-hexadec-9-ene-yl or Z- or E-octadec-9-ene-yl.

C₃-C₁₂-alkine-yl is for example propargyl, but-2-ine-yl or undec-11-ine-yl.

C₄-C₈-cycloalkyl is for example cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Preferred is C₅-C₇-cycloalkyl, in particular cyclohexyl.

C₄-C₈-cycloalkyl, which is substituted by one to three C₁-C₄-alkyl, is for example 3,4-dimethyl-cyclopentyl, 4-methyl-cyclohexyl, 2-methyl-cyclohexyl, 3,5-dimethyl-cyclohexyl or 4-(1-methyl-ethyl)-cyclohexyl or 5-methyl-2-(1-methyl-ethyl)-cyclohexyl.

C₆-C₁₀-aryl is for example phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 4-(1,1-dimethylethyl)-phenyl, biphenyl-4-yl, napthalen-1-yl or napthalen-2-yl. Preferred is phenyl.

Bicyclic or tricyclic C₅-C₂₀-alkyl is for example 2-methyl-bicyclo[2.2.1]heptane-1′-yl, 1,7,7-trimethylbicyclo[2.2.1]heptane-2-yl, adamantane-yl, 1-methyl-adamantane-1′-yl or 1,3-dimethyl-adamantane-1′-yl.

C₄-C₈-cycloalkyl-C₁-C₄-alkyl is for example 2-(cyclopentyl)-ethyl, cyclohexyl-methyl, 2-(cyclohexyl)-ethyl, 2-(cyclohexyl)-1-methyl-ethyl or (cycloheptyl)-methyl.

C₆-C₁₄-aryl-C₁-C₄-alkyl is for example benzyl, 4-methyl-benzyl, 2-phenyl-ethyl, 3,5-dimethylbenzyl, 1-phenyl-1,1-dimethyl-methyl, 3-phenyl-propyl, 3-phenyl-2-methyl-propyl, 3,5-di-tert-butyl-benzyl or biphenyl-4-yl-methyl.

C₂-C₁₂-alkyl, which is substituted by one or more hydroxyl groups, is for example 2-hydroxy-ethyl, 3-hydroxy-propyl, 2-hydroxy-2-methyl-ethyl, 2,2-dimethyl-3-hydroxy-propyl, 4-hydroxy-butyl, 6-hydroxy-hexyl, 2,3-dihydroxy-propyl, 2-hydroxy-butyl, 2-hydroxy-hexyl,1,3-dihydroxy-propane-2-yl, 2,3,4,5-tetrahydroxy-pentyl or 2,3,4,5,6-pentahydroxy-hexyl. Preferred is C₂-C₈-alkyl, which is substituted by one hydroxyl group. Preferred in particular is 2-hydroxy-ethyl or 2-hydroxy-2-methyl-ethyl.

C₁-C₈-alkoxy is for example methoxy, ethoxy, n-propoxy, 1-methyl-ethoxy, n-butoxy, 1-methyl-propoxy, 2-methyl-propoxy, 1,1-dimethyl-ethoxy, n-pentoxy, 1-methyl-butoxy, 2-methyl-butoxy, 3-methyl-butoxy, n-hexane-oxy, n-heptane-oxy, n-octane-oxy or 1-methyl-heptane-oxy. C₁-C₄-alkoxy is preferred.

Phenyl, which is unsubstituted or substituted by one or more C₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen, is for example phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 3,5-dimethyl-phenyl, 4-methyl-phenyl, 3-(1-methyl-propyl)-phenyl, 4-(1-methyl-propyl)-phenyl, 4-(1,1-dimethyl-ethyl)-phenyl, 4-(1,1,3,3-tetramethyl-butyl)-phenyl, 4-cyclohexyl-phenyl, biphenyl-4-yl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 4-ethoxy-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl or 4-bromo-phenyl. Preferred is phenyl, which is unsubstituted or substituted by one C₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen. Preferred is phenyl, which is unsubstituted.

C₄-C₁₂-alkyl, which is interrupted by one or more oxygen atoms, is for example 2-ethoxy-ethyl, 2-(2-methoxy-ethoxy)-ethyl, 2-n-butoxy-ethyl, 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl, 2-[2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy]-ethyl, 2-(2-methoxy-1-methyl-ethoxy)-1-methyl-ethyl, 3-(n-propoxy)-propyl, 2-(2-hydroxy-ethoxy)-ethyl, 2-[2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy]-ethyl or 2-[2-(2-hydroxy-2-methyl-ethoxy)-2-methyl -ethoxy]-2-methyl-ethyl.

C₄-C₁₆-alkyl, which is interrupted by one sulfur atom, is for example 3-thiaundecyl or 3-thiapentadecyl.

Halogen is for example a chlorine atom, a bromine atom or iodine atom. Preferred is a chlorine atom.

C₂-C₁₂-alkylene is for example ethylene, 1-methyl-ethane-1,2-diyl, n-propylene, n-butylene, 2-methyl-butane-1,4-diyl, hexamethylene or decane-1,10-diyl.

C₄-C₈-cycloalkylene is for example cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cyclohexane-1,2-diyl, cyclooctane-1,2-diyl or cycloheptane-1,3-diyl.

C₆-C₁₄-arylene is for example 1,3-phenylene, 1,4-phenylene, 2,3-dimethyl-benzene-1,4-diyl, biphenyl-4,4′-diyl, naphtalene-2,6-diyl or naphthalene-1,4-diyl.

C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene) is for example cyclopentane-1,3-bismethylene, cyclohexane-1,4-bismethylene, cyclohexane-1,3-bismethylene, cyclohexane-1,4-bisethylene or cyclohexane-1,4-bis(1-methyl-ethane-1,2-diyl).

C₆-C₁₄-arene-bis-(C₁-C₄-alkylene) is for example benzene-1,3-bismethylene, benzene-1,4-bismethylene, napthaline-1,4-bismethylene, napthaline-2,6-bismethylene, 5-methyl-benzene-1,3-bismethylene, 5-tert-butyl-benzene-1,3-bismethylene, benzene-1,4-bisethylene, benzene-1,4-bis-(1-methyl-ethan-1,2-diyl) or biphenyl-4,4′-bismethylene.

C₃-C₆-alkylene, which is substituted by one or more hydroxyl groups, is for example 2-hydroxy-propane-1,3-diyl, 1-hydroxymethyl-ethane-1,2-diyl, 2,3,4-trihydroxypentane-1,5-diyl, 2,3,4-trihydroxyhexane-1,6-diyl or 2,3,4,5-tetrahydroxy-hexane-1,6-diyl.

C₄-C₁₂-alkylene, which is interrupted by one or more oxygen atoms, is for example 2-ethoxyethane-1,2′-diyl, —(CH₂CH₂—O)₂—CH₂CH₂—, —(CH₂CH₂—O)₃—CH₂CH₂—, —CH(CH₃)CH₂—O—CH(CH₃)CH₂—, —[CH(CH₃)CH₂—O]₂—CH(CH₃)CH₂—, —CH₂CH₂CH₂CH₂—O—CH₂CH₂CH₂CH₂— or —(CH₂CH₂CH₂CH₂—O)₂—CH₂CH₂CH₂CH₂—.

C₄-C₈-alkylene, which is interrupted by one sulfur atom, is for example —CH₂CH₂—S—CH₂CH₂—, —CH₂CH₂CH₂—S—CH₂CH₂CH₂— or —CH(CH₃)CH₂—S—CH₂—CH(CH₃)—.

3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl is for example —CH₂CH₂—N(CH₃)—CH₂CH₂— or —CH₂CH₂—N(CH₂—C(CH₃)₂—CH₂—CH₃)—CH₂CH₂—.

4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl is for example —CH₂CH₂CH₂—N(CH₃)—CH₂CH₂CH₂— or —CH₂CH₂—N(CH₂—C(CH₃)₂—CH₂—CH₃)—CH₂CH₂CH₂—.

A 5-, 6- or 7-membered saturated heterocycle is for example pyrrolidine, piperidine, azepane, morpholine or 2,6-dimethyl-morpholine.

The sign ‘star’ (=-*) indicates the free bonding valence of the carbon atom at the depicted radicals below.

Hexahydro-furo[3,2-b]furane-3,6-diyl is a divalent radical as depicted:

Piperazine-N,N′-biscarbonyl is a divalent radical as depicted:

1-Ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl is a divalent radical as depicted:

C₃-C₁₂-alkane-tri-(oxycarbonyl) is a trivalent radical and for example propane-1,2,3-tri-(oxycarbonyl) as depicted:

2-methyl-propane-1,2,3-tri-(oxycarbonyl) as depicted:

2-methyl-butane-1,2,1′-tri-(oxycarbonyl) as depicted:

2,2-dimethyl-butane-1,1′,1″-tri-(oxycarbonyl) as depicted:

or

2,2-dimethyl-pentane-1,1′,1″-tri-(oxycarbonyl) as depicted:

3-Ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl) is a trivalent radical as depicted:

1,4,7-Triazaheptane-1,4,7-tricarbonyl is a trivalent radical as depicted:

1,4,8-Triazaoctane-1,4,8-tricarbonyl is a trivalent radical as depicted:

1,5,9-Triazanonane-1,5,9-tricarbonyl is a trivalent radical as depicted:

C₄-C₁₆-alkane-tetra-(oxycarbonyl) is a tetravalent radical and for example 2,2-dimethyl-propane-1,3,1′,1″-tetra-(oxycarbonyl) as depicted:

butane-1,2,3,4-tetra-(oxycarbonyl) as depicted:

hexane-1,3,4,6-tetra-(oxycarbonyl) as depicted:

or

octane-1,3,6,8-tetra-(oxycarbonyl) as depicted:

1,4,7,10-Tetraazadecane-1,4,7,10-tetracarbonyl is a tetravalent radical as depicted:

1,4,8,11-Tetraazaundecane-1,4,8,11-tetracarbonyl is a tetravalent radical as depicted:

1,5,8,12-Tetraazadodecane-1,5,8,12-tetracarbonyl is a tetravalent radical as depicted:

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen, with the proviso that at least R₁ or R₅ is H and at least     R₆ or R₁₀ is H.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄ and R₅ are independently from each other H,     C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen; -   R₆ is R₁; R₇ is R₂; R₈ is R₃; R₉ is R₄ and R₁₀ is R₅.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄ and R₅ are independently from each other H,     C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen, with     the proviso that at least R₁ is H; -   R₆ is R₁; R₇ is R₂; R₈ is R₃; R₉ is R₄ and R₁₀ is R₅.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, methyl or methoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and -   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl,     C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and -   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl, phenyl     or C₁-C₄-alkoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and -   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl or     C₁-C₄-alkoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; and -   R₃ and R₈ are independently from each other H or methoxy.

Preferred is a compound of formula I, wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are H.

Preferred is a compound of formula I, wherein

-   R′₃ is H; and -   R″₂ and R″₃ are H.

Preferred is a compound of formula I, wherein

-   n is 1, 2 or 3.

Preferred is a compound of formula I, wherein

-   n is 1 or 2.

Preferred is a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is     substituted by one or more C₁-C₈-alkyl, C₁-C₄-alkoxy,     C₅-C₇-cycloalkyl or halogen, —H or —SO₂-phenyl.

Preferred is a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, —H or —SO₂-phenyl.

Preferred is a compound of formula I, wherein

-   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl); -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl).

Preferred is a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —CN, phenyl, which is unsubstituted or substituted     by one or more C₁-C₈-alkyl, C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or     halogen, —H or —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl); -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl).

Preferred is a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is     unsubstituted or substituted by one or more C₁-C₈-alkyl,     C₁-C₄-alkoxy, C₅-C₇-cycloalkyl or halogen, —H or —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)— or —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)—; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl) or     3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl); -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl); -   n is 1, 2, 3 or 4; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkinyl,     C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to     three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or     tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which     is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which     is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is     interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,     which is substituted by a hydroxyl group,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     5-, 6- or 7-membered saturated heterocycle; -   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,     C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms,     hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or     1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and -   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,     C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms,     3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁ or —C(═O)—N(R′₂)(R′₃); -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or     piperazine-N,N′-biscarbonyl; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl); -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl); -   n is 1, 2, 3 or 4; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,     C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to     three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or     tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which     is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which     is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is     interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,     which is substituted by a hydroxyl group,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     5-, 6- or 7-membered saturated heterocycle; -   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,     C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms, C₄-C₈-alkylene, which is     interrupted by a sulfur atom; and -   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,     C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms,     3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a composition, which comprise a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is     unsubstituted or substituted by one to three C₁-C₈-alkyl or     C₁-C₄-alkoxy, —H or —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or     piperazine-N,N′-biscarbonyl; -   when n is 3 -   A is propane-1,2,3-tri-(oxycarbonyl),     2-methyl-propane-1,2,3-tri-(oxycarbonyl),     2-methyl-butane-1,2,1′-tri-(oxycarbonyl),     2,2-dimethyl-butane-1,1′,1″-tri-(oxycarbonyl),     2,2-dimethyl-pentane-1,1′,1″-tri-(oxycarbonyl),     3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl); -   when n is 4 -   A is 2,2-dimethyl-propane-1,3,1′,1″-tetra-(oxycarbonyl); -   n is 1, 2, 3 or 4; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, phenyl or C₁-C₄-alkoxy with the proviso     that at least R₁ or R₅ is H and at least R₆ or R₁₀ is H; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is     unsubstituted or substituted by one C₁-C₄-alkyl,     C₅-C₇-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₀-aryl-C₁-C₄-alkyl, C₄-C₁₂-alkyl,     which is interrupted by one or more oxygen atoms,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted or     substituted by one C₁-C₄-alkyl, C₆-C₁₀-aryl,     C₅-C₇-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₀-aryl-C₁-C₄-alkyl,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     pyrrolidine, a piperidine or a morpholine; -   R″₁ and R″₂ independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted or     substituted by one C₁-C₄-alkyl, C₅-C₇-cycloalkyl-C₁-C₄-alkyl,     C₆-C₁₀-aryl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene,     C₅-C₇-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₀-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl or     1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and -   Z₂ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene, C₆-C₁₄-arylene,     C₅-C₇-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₀-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms,     3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a composition, which comprise a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, which is     unsubstituted or substituted by one or two C₁-C₈-alkyl or     C₁-C₄-alkoxy, —H or —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or     piperazine-N,N′-biscarbonyl; -   when n is 3 -   A is propane-1,2,3-tri-(oxycarbonyl),     2-methyl-propane-1,2,3-tri-(oxycarbonyl),     2-methyl-butane-1,2,1′-tri-(oxycarbonyl),     2,2-dimethyl-butane-1,1′,1″-tri-(oxycarbonyl),     2,2-dimethyl-pentane-1,1′,1″-tri-(oxycarbonyl); -   when n is 4 -   A is 2,2-dimethyl-propane-1,3,1′,1″-tetra-(oxycarbonyl); -   n is 1, 2, 3 or 4; -   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; -   R₃ and R₈ are independently from each other H, C₁-C₈-alkyl,     C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is     unsubstituted, C₅-C₇-cycloalkyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl,     C₄-C₁₂-alkyl, which is interrupted by one or more oxygen atoms,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted,     C₆-C₁₀-aryl, C₅-C₇-cycloalkyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     pyrrolidine, a piperidine or a morpholine; -   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₅-C₇-cycloalkyl, which is unsubstituted,     C₅-C₇-cycloalkyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene,     C₅-C₇-cycloalkane-bis-(C₁-C₄-alkylene),     benzene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is substituted     by one or more hydroxyl groups, C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl or     1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and -   Z₂ is C₂-C₁₂-alkylene, C₅-C₇-cycloalkylene, C₆-C₁₄-arylene,     C₅-C₇-cycloalkane-bis(C₁-C₄-alkylene), benzene-bis-(C₁-C₄-alkylene),     C₄-C₁₂-alkylene, which is interrupted by one or more oxygen atoms,     3-(C₁-C₄-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₄-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a composition, which comprise a compound of formula I, wherein

-   n is 1; -   A is —CN, phenyl or —H; and -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen.

Preferred is a composition, which comprise a compound of formula I, wherein at formula I

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃), —CN, phenyl, —H or     —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—; -   n is 1 or 2; -   R₁, R₂, R₄, R₅, R₆, R₇, R₉ and R₁₀ are H; -   R₃ and R₈ are independently from each other H or C₁-C₄-alkoxy; -   R′₁ is H, C₁-C₁₂-alkyl, C₅-C₇-cycloalkyl, which is unsubstituted,     phenyl-C₁-C₄-alkyl,     1-(C₁-C₆-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₁₂-alkyl,     C₅-C₇-cycloalkyl, which is unsubstituted, C₆-C₁₀-aryl,     phenyl-C₁-C₄-alkyl, 1-(C₁-C₆-alkyl)-2,2,6,6-tetramethyl     -piperidine-4-yl or     1-(C₁-C₆-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     pyrrolidine, a piperidine or a morpholine; and -   Z₁ is C₅-C₇-cycloalkylene.

Preferred is a composition, which comprise a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OCH₃, —CN, phenyl or —H; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—; -   n is 1 or 2; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are H; and -   Z₁ is cyclo-hexane-1,4-diyl.

The organic material of the present invention is susceptible to oxidative, thermal or light-induced degradation.

Examples of an organic material are:

-   1. Polymers of monoolefins and diolefins, for example polypropylene,     polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene,     polyvinylcyclohexane, polyisoprene or polybutadiene, as well as     polymers of cycloolefins, for instance of cyclopentene or     norbornene, polyethylene (which optionally can be crosslinked), for     example high density polyethylene (HDPE), high density and high     molecular weight polyethylene (HDPE-HMW), high density and ultrahigh     molecular weight polyethylene (HDPE-UHMW), medium density     polyethylene (MDPE), low density polyethylene (LDPE), linear low     density polyethylene (LLDPE), (VLDPE) and (ULDPE).

Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:

-   -   a) radical polymerisation (normally under high pressure and at         elevated temperature).     -   b) catalytic polymerisation using a catalyst that normally         contains one or more than one metal of groups IVb, Vb, VIb or         VIII of the Periodic Table. These metals usually have one or         more than one ligand, typically oxides, halides, alcoholates,         esters, ethers, amines, alkyls, alkenyls and/or aryls that may         be either π- or σ-coordinated. These metal complexes may be in         the free form or fixed on substrates, typically on activated         magnesium chloride, titanium(III) chloride, alumina or silicon         oxide. These catalysts may be soluble or insoluble in the         polymerisation medium. The catalysts can be used by themselves         in the polymerisation or further activators may be used,         typically metal alkyls, metal hydrides, metal alkyl halides,         metal alkyl oxides or metal alkyloxanes, said metals being         elements of groups Ia, IIa and/or IIIa of the Periodic Table.         The activators may be modified conveniently with further ester,         ether, amine or silyl ether groups. These catalyst systems are         usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta),         TNZ (DuPont), metallocene or single site catalysts (SSC).

-   2. Mixtures of the polymers mentioned under 1), for example mixtures     of polypropylene with polyisobutylene, polypropylene with     polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of     different types of polyethylene (for example LDPE/HDPE).

-   3. Copolymers of monoolefins and diolefins with each other or with     other vinyl monomers, for example ethylene/propylene copolymers,     linear low density polyethylene (LLDPE) and mixtures thereof with     low density polyethylene (LDPE), propylene/but-1-ene copolymers,     propylene/isobutylene copolymers, ethylene/but-1-ene copolymers,     ethylene/hexene copolymers, ethylene/methylpentene copolymers,     ethylene/heptene copolymers, ethylene/octene copolymers,     ethylene/vinylcyclohexane copolymers, ethylene/cycloolefin     copolymers (e.g. ethylene/norbornene like COC), ethylene/1-olefins     copolymers, where the 1-olefin is generated in-situ;     propylene/butadiene copolymers, isobutylene/isoprene copolymers,     ethylene/vinylcyclohexene copolymers, ethylene/alkyl acrylate     copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl     acetate copolymers or ethylene/acrylic acid copolymers and their     salts (ionomers) as well as terpolymers of ethylene with propylene     and a diene such as hexadiene, dicyclopentadiene or     ethylidene-norbornene; and mixtures of such copolymers with one     another and with polymers mentioned in 1) above, for example     polypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinyl     acetate copolymers (EVA), LDPE/ethylene-acrylic acid copolymers     (EAA), LLDPE/EVA, LLDPE/EAA and alternating or random     polyalkylene/carbon monoxide copolymers and mixtures thereof with     other polymers, for example polyamides.

A special copolymer of two monoolefins is a pipe grade polypropylene random copolymer, which is obtainable from the polymerization of more than 90% by weight of propylene and of less than 10% by weight, typically between 2 and 6% by weight, of ethylene.

4. Hydrocarbon resins (for example C₅-C₉) including hydrogenated modifications thereof (e.g. tackifiers) and mixtures of polyalkylenes and starch.

Homopolymers and copolymers from 1.)-4.) may have any stereostructure including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

-   5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene). -   6. Aromatic homopolymers and copolymers derived from vinyl aromatic     monomers including styrene, α-methylstyrene, all isomers of vinyl     toluene, especially p-vinyl-toluene, all isomers of ethyl styrene,     propyl styrene, vinyl biphenyl, vinyl naphthalene, and vinyl     anthracene, and mixtures thereof. Homopolymers and copolymers may     have any stereostructure including syndiotactic, isotactic,     hemi-isotactic or atactic; where atactic polymers are preferred.     Stereoblock polymers are also included. -   6a. Copolymers including aforementioned vinyl aromatic monomers and     comonomers selected from ethylene, propylene, dienes, nitriles,     acids, maleic anhydrides, maleimides, vinyl acetate and vinyl     chloride or acrylic derivatives and mixtures thereof, for example     styrene/butadiene, styrene/acrylonitrile, styrene/ethylene     (interpolymers), styrene/alkyl methacrylate, styrene/butadiene/alkyl     acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic     anhydride, styrene/acrylonitrile/methyl acrylate; mixtures of high     impact strength of styrene copolymers and another polymer, for     example a polyacrylate, a diene polymer or an     ethylene/propylene/diene terpolymer; and block copolymers of styrene     such as styrene/butadiene/styrene, styrene/isoprene/styrene,     styrene/ethylene/butylene/styrene or     styrene/ethylene/propylene/styrene. -   6b. Hydrogenated aromatic polymers derived from hydrogenation of     polymers mentioned under 6.), especially including     polycyclohexylethylene (PCHE) prepared by hydrogenating atactic     polystyrene, often referred to as polyvinylcyclohexane (PVCH). -   6c. Hydrogenated aromatic polymers derived from hydrogenation of     polymers mentioned under 6a.).

Homopolymers and copolymers may have any stereostructure including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

-   7. Graft copolymers of vinyl aromatic monomers such as styrene or     α-methylstyrene, for example styrene on polybutadiene, styrene on     polybutadiene-styrene or polybutadiene-acrylonitrile copolymers;     styrene and acrylonitrile (or methacrylonitrile) on polybutadiene;     styrene, acrylonitrile and methyl methacrylate on polybutadiene;     styrene and maleic anhydride on polybutadiene; styrene,     acrylonitrile and maleic anhydride or maleimide on polybutadiene;     styrene and maleimide on polybutadiene; styrene and alkyl acrylates     or methacrylates on polybutadiene; styrene and acrylonitrile on     ethylene/propylene/diene terpolymers; styrene and acrylonitrile on     polyalkyl acrylates or polyalkyl methacrylates, styrene and     acrylonitrile on acrylate/butadiene copolymers, as well as mixtures     thereof with the copolymers listed under 6), for example the     copolymer mixtures known as ABS, MBS, ASA or AES polymers. -   8. Halogen-containing polymers such as polychloroprene, chlorinated     rubbers, chlorinated and brominated copolymer of     isobutylene-isoprene (halobutyl rubber), chlorinated or     sulfochlorinated polyethylene, copolymers of ethylene and     chlorinated ethylene, epichlorohydrin homo- and copolymers,     especially polymers of halogen-containing vinyl compounds, for     example polyvinyl chloride, polyvinylidene chloride, polyvinyl     fluoride, polyvinylidene fluoride, as well as copolymers thereof     such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl     acetate or vinylidene chloride/vinyl acetate copolymers. -   9. Polymers derived from α,β-unsaturated acids and derivatives     thereof such as polyacrylates and polymethacrylates; polymethyl     methacrylates, polyacrylamides and polyacrylonitriles,     impact-modified with butyl acrylate. -   10. Copolymers of the monomers mentioned under 9) with each other or     with other unsaturated monomers, for example acrylonitrile/butadiene     copolymers, acrylonitrite/alkyl acrylate copolymers,     acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide     copolymers or acrylonitrile/alkyl methacrylate/butadiene     terpolymers. -   11. Polymers derived from unsaturated alcohols and amines or the     acyl derivatives or acetals thereof, for example polyvinyl alcohol,     polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl     maleate, polyvinyl butyral, polyallyl phthalate or polyallyl     melamine; as well as their copolymers with olefins mentioned in 1)     above. -   12. Homopolymers and copolymers of cyclic ethers such as     polyalkylene glycols, polyethylene oxide, polypropylene oxide or     copolymers thereof with bisglycidyl ethers. -   13. Polyacetals such as polyoxymethylene and those polyoxymethylenes     which contain ethylene oxide as a comonomer; polyacetals modified     with thermoplastic polyurethanes, acrylates or MBS. -   14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene     oxides with styrene polymers or polyamides. -   15. Polyurethanes, for example polyurethanes synthesized from a     polyol and an aliphatic or aromatic polyisocyanate such as     polyurethanes derived from hydroxyl-terminated polyethers,     polyesters or polybutadienes on the one hand and aliphatic or     aromatic polyisocyanates on the other, as well as precursors     thereof. Hydroxyl-terminated polyethers are known and are prepared,     for example, by polymerizing epoxides such as ethylene oxide,     propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or     epichlorohydrin with themselves, for example in the presence of BF₃,     or by addition reaction of these epoxides, alone or as a mixture or     in succession, with starting components containing reactive hydrogen     atoms, such as water, alcohols, ammonia or amines, for example     ethylene glycol, propylene 1,3- and 1,2-glycol, trimethylolpropane,     4,4′-dihydroxydiphenylpropane, aniline, ethanolamine or     ethylenediamine. Sucrose polyethers are also suitable in accordance     with the invention. In many cases preference is given to those     polyethers which predominantly (up to 90% by weight, based on all     the OH groups present in the polyether) contain primary OH groups.     Furthermore, polyethers modified by vinyl polymers, as are formed,     for example, by polymerizing styrene and acrylonitrile in the     presence of polyethers, are suitable, as are polybutadienes     containing OH groups.

In particular, a polyol compound has a molecular weight of 400-10000, especially 800 to 10000, and is a polyhydroxy compound, especially containing from 2 to 8 hydroxyl groups, especially from 2 to 4.

Suitable polyisocyanates are aliphatic or aromatic, for example ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane 1,3-diisocyanate, cyclohexane 1,3- and -1,4-diisocyanate and also any desired mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4- and 2,6-hexahydrotolylene diisocyanate and also any desired mixtures of these isomers, hexahydro-1,3- and/or -1,4-phenylene diisocyanate, perhydro-2,4′- and/or -4,4′-diphenylmethanediisocyanate, 1,3- and 1,4-phenylene diisocyanate, 2,4- and 2,6-tolylene diisocyanate, and also any desired mixtures of these isomers, diphenylmethane 2,4′- and/or -4,4′-diisocyanate, naphthylene 1,5-diisocyanate, triphenylmethane 4,4′,4″-triisocyanate, polyphenyl-polymethylene polyisocyanates as are obtained by aniline-formaldehyde condensation followed by phosgenization, m- and p-isocyanatophenylsulfonyl isocyanates, perchlorinated aryl polyisocyanates, polyisocyanates containing carbodiimide groups, polyisocyanates containing allophanate groups, polyisocyanates containing isocyanurate groups, polyisocyanates containing urethane groups, polyisocyanates containing acylated urea groups, polyisocyanates containing biuret groups, polyisocyanates containing ester groups, reaction products of the abovementioned isocyanates with acetals, and polyisocyanates containing polymeric fatty acid radicals.

It is also possible to employ the isocyanate group-containing distillation residues, as they are or dissolved in one or more of the abovementioned polyisocyanates, which are obtained in the course of the industrial preparation of isocyanates. It is additionally possible to use any desired mixtures of the abovementioned polyisocyanates.

Preferred are 2,4- or 2,6-tolylene diisocyanate and any desired mixtures of these isomers (“TDI”), polyphenyl-polymethylene-polyisocyanates as prepared by aniline-formaldehyde condensation followed by phosgenization (“crude MDI”) or polyisocyanates containing carbodiimide, urethane, allophanate, isocyanurate, urea or biuret groups (“modified polyisocyanates”).

The polyurethanes can be homogeneous polyurethanes or cellular.

-   16. Polyamides and copolyamides derived from diamines and     dicarboxylic acids and/or from aminocarboxylic acids or the     corresponding lactams, for example polyamide 4, polyamide 6,     polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide     12, aromatic polyamides starting from m-xylene diamine and adipic     acid; polyamides prepared from hexamethylenediamine and isophthalic     or/and terephthalic acid and with or without an elastomer as     modifier, for example poly-2,4,4,-trimethylhexamethylene     terephthalamide or poly-m-phenylene isophthalamide; and also block     copolymers of the aforementioned polyamides with polyolefins, olefin     copolymers, ionomers or chemically bonded or grafted elastomers; or     with polyethers, e.g. with polyethylene glycol, polypropylene glycol     or polytetramethylene glycol; as well as polyamides or copolyamides     modified with EPDM or ABS; and polyamides condensed during     processing (RIM polyamide systems). -   17. Polyureas, polyimides, polyamide-imides, polyetherimides,     polyesterimides, polyhydantoins and polybenzimidazoles. -   18. Polyesters derived from dicarboxylic acids and diols and/or from     hydroxycarboxylic acids or the corresponding lactones or lactides,     for example polyethylene terephthalate, polybutylene terephthalate,     poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene     naphthalate and polyhydroxybenzoates as well as copolyether esters     derived from hydroxyl-terminated polyethers, and also polyesters     modified with polycarbonates or MBS. Copolyesters may comprise, for     example—but are not limited to—polybutylenesuccinate/terephtalate,     polybutyleneadipate/terephthalate,     polytetramethyleneadipate/terephthalate,     polybutylensuccinate/adipate, polybutylensuccinate/carbonate,     poly-3-hydroxybutyrate/octanoate copolymer,     poly-3-hydroxybutyrate/hexanoate/decanoate terpolymer. Furthermore,     aliphatic polyesters may comprise, for example—but are not limited     to—the class of poly(hydroxyalkanoates), in particular,     poly(propiolactone), poly(butyrolactone), poly(pivalolactone),     poly(valerolactone) and poly(caprolactone), polyethylenesuccinate,     polypropylenesuccinate, polybutylenesuccinate,     polyhexamethylenesuccinate, polyethyleneadipate,     polypropyleneadipate, polybutyleneadipate, polyhexamethyleneadipate,     polyethyleneoxalate, polypropyleneoxalate, polybutyleneoxalate,     polyhexamethyleneoxalate, polyethylenesebacate,     polypropylenesebacate, polybutylenesebacate and polylactic acid     (PLA) as well as corresponding polyesters modified with     polycarbonates or MBS. The term “polylactic acid (PLA)” designates a     homo-polymer of preferably poly-L-lactide and any of its blends or     alloys with other polymers; a co-polymer of lactic acid or lactide     with other monomers, such as hydroxy-carboxylic acids, like for     example glycolic acid, 3-hydroxy-butyric acid, 4-hydroxy-butyric     acid, 4-hydroxy-valeric acid, 5-hydroxy-valeric acid,     6-hydroxy-caproic acid and cyclic forms thereof; the terms “lactic     acid” or “lactide” include L-lactic acid, D-lactic acid, mixtures     and dimers thereof, i.e. L-lactide, D-lactide, meso-lacide and any     mixtures thereof. -   19. Polycarbonates and polyester carbonates. -   20. Polyketones. -   21. Polysulfones, polyether sulfones and polyether ketones. -   22. Crosslinked polymers derived from aldehydes on the one hand and     phenols, ureas and melamines on the other hand, such as     phenol/formaldehyde resins, urea/formaldehyde resins and     melamine/formaldehyde resins. -   23. Drying and non-drying alkyd resins. -   24. Unsaturated polyester resins derived from copolyesters of     saturated and unsaturated dicarboxylic acids with polyhydric     alcohols and vinyl compounds as crosslinking agents, and also     halogen-containing modifications thereof of low flammability. -   25. Crosslinkable acrylic resins derived from substituted acrylates,     for example epoxy acrylates, urethane acrylates or polyester     acrylates. -   26. Alkyd resins, polyester resins and acrylate resins crosslinked     with melamine resins, urea resins, isocyanates, isocyanurates,     polyisocyanates or epoxy resins. -   27. Crosslinked epoxy resins derived from aliphatic, cycloaliphatic,     heterocyclic or aromatic glycidyl compounds, e.g. products of     diglycidyl ethers of bisphenol A and bisphenol F, which are     crosslinked with customary hardeners such as anhydrides or amines,     with or without accelerators. -   28. Natural polymers such as cellulose, rubber, gelatin and     chemically modified homologous derivatives thereof, for example     cellulose acetates, cellulose propionates and cellulose butyrates,     or the cellulose ethers such as methyl cellulose; as well as rosins     and their derivatives. -   29. Blends of the aforementioned polymers (polyblends), for example     PP/EPDM, polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS,     PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic     PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA     6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or     PBT/PET/PC. -   30. Naturally occurring and synthetic organic materials which are     pure monomeric compounds or mixtures of such compounds, for example     mineral oils, animal and vegetable fats, oil and waxes, or oils,     fats and waxes based on synthetic esters (e.g. phthalates, adipates,     phosphates or trimellitates) and also mixtures of synthetic esters     with mineral oils in any weight ratios, typically those used as     spinning compositions, as well as aqueous emulsions of such     materials. -   31. Aqueous emulsions of natural or synthetic rubber, e.g. natural     latex or latices of carboxylated styrene/butadiene copolymers.

A polymer can be natural, semi-synthetic or synthetic. A natural polymer is isolated from a natural source without further synthetic modifications. A synthetic polymer does not contain a polymer part isolated from a natural source. A semi-synthetic polymer contains at least one natural polymer part, wherein the natural polymer part can be synthetically modified and/or reacted with monomers to form the semi-synthetic polymer.

A polymer can be thermoplastic, i.e. it can be shaped into a new form at an elevated temperature, for example at a temperature in the range from 150° C. to 340° C.

Preferred is a composition, which comprises as component a) an organic material, wherein the organic material is selected from the group consisting of a polymer, a wax, a mineral oil and a fat, and a component b).

Preferred is a composition, which comprises as component a) a polymer, in particular a semi-synthetic or synthetic polymer, and as component b) a compound of formula I.

Preferred is a composition, which comprises as component a) a semi-synthetic or synthetic polymer.

Preferred is a composition, which comprises as component a) a thermoplastic polymer.

Preferred is a composition, which comprises as component a) a polymer, which is synthetic and thermoplastic.

Preferred is a composition, which comprises as component a) a polyolefin, a polyether polyol or a polyurethane.

The employed amount of component b) in regard to component a) varies with the particular organic material and the desired degree of protection.

Preferred is a composition, which comprises a component a) and a component b), wherein component b) is contained in an amount of 0.0005% to 10%, in particular from 0.001 to 2%, especially from 0.005 to 1%, based on the weight of component a).

Optionally, a composition comprising a component a) and a component b) contains as component c) a further additive.

A further additive can be selected from the following list:

-   1. Antioxidants -   1.1. Alkylated monophenols, for example     2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol,     2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol,     2,6-di-tert-butyl-4-isobutylphenol,     2,6-dicyclopentyl-4-methylphenol,     2-(α-methylcyclohexyl)-4,6-dimethylphenol,     2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,     2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are     linear or branched in the side chains, for example     2,6-di-nonyl-4-methylphenol,     2,4-dimethyl-6-(1′-methylundec-1′-yl)phenol,     2,4-dimethyl-6-(1′-methylheptadec-1′-yl)phenol,     2,4-dimethyl-6-(1′-methyltridec-1′-yl)phenol,     2,4-dimethyl-6-(1′-methyl-1′-tetradecyl-methyl)-phenol and mixtures     thereof. -   1.2. Alkylthiomethylphenols, for example     2,4-dioctylthiomethyl-6-tert-butylphenol,     2,4-dioctylthiomethyl-6-methylphenol,     2,4-dioctylthiomethyl-6-ethylphenol,     2,6-di-dodecylthiomethyl-4-nonylphenol. -   1.3. Hydroquinones and alkylated hydroquinones, for example     2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone,     2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol,     2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole,     3,5-di-tert-butyl-4-hydroxyanisole,     3,5-di-tert-butyl-4-hydroxyphenyl stearate,     bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate. -   1.4. Tocopherols, for example α-tocopherol, β-tocopherol,     γ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E). -   1.5. Hydroxylated thiodiphenyl ethers, for example     2,2′-thiobis(6-tert-butyl-4-methylphenol),     2,2′-thiobis(4-octylphenol),     4,4′-thiobis(6-tert-butyl-3-methylphenol),     4,4′-thiobis(6-tert-butyl-2-methylphenol),     4,4′-thiobis(3,6-di-sec-amylphenol),     4,4′-bis(2,6-dimethyl-4-hydroxyphenyl)disulfide. -   1.6. Alkylidenebisphenols, for example     2,2′-methylenebis(6-tert-butyl-4-methylphenol),     2,2′-methylenebis(6-tert-butyl-4-ethylphenol),     2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl) phenol],     2,2′-methylenebis(4-methyl-6-cyclohexylphenol),     2,2′-methylenebis(6-nonyl-4-methylphenol),     2,2′-methylenebis(4,6-di-tert-butylphenol),     2,2′-ethylidenebis(4,6-di-tert-butylphenol),     2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol),     2,2′-methylenebis[6-(α-methylbenzyl)-4-nonylphenol],     2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol],     4,4′-methylenebis(2,6-di-tert-butylphenol),     4,4′-methylenebis(6-tert-butyl-2-methylphenol),     1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,     2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol,     1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,     1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane,     ethylene glycol     bis[3,3-bis(3′-tert-butyl-4′-hydroxyphenyl)-butyrate],     bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene,     bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate,     1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane,     2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-propane,     2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane,     1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane. -   1.7. O—, N— and S-benzyl compounds, for example     3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether,     octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate,     tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate,     tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine,     bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate,     bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide,     isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate. -   1.8. Hydroxybenzylated malonates, for example     dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate,     di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate,     di-dodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,     bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate. -   1.9. Aromatic hydroxybenzyl compounds, for example     1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,     1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene,     2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol. -   1.10. Triazine compounds, for example     2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,     2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,     2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine,     2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine,     1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,     1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate,     2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine,     1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine,     1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate. -   1.11. Benzylphosphonates, for example     dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate,     diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,     dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,     dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the     calcium salt of the monoethyl ester of     3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid. -   1.12. Acylaminophenols, for example 4-hydroxylauranilide,     4-hydroxystearanilide, octyl     N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate. -   1.13. Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid     with mono- or polyhydric alcohols, for example with methanol,     ethanol, n-octanol, i-octanol, octadecanol, a mixture of linear and     branched C₁₃-C₁₅-alkanol, 1,6-hexanediol, 1,9-nonanediol, ethylene     glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol,     diethylene glycol, triethylene glycol, pentaerythritol,     tris(hydroxylethyl)isocyanurate, N,N′-bis-(hydroxylethyl)oxamide,     3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,     trimethylolpropane,     4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane. -   1.14. Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic     acid with mono- or polyhydric alcohols, for example with methanol,     ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol,     1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol,     thiodiethylene glycol, diethylene glycol, triethylene glycol,     pentaerythritol, tris(hydroxyethyl)isocyanurate,     N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,     trimethylhexanediol, trimethylolpropane,     4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;     3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane. -   1.15. Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid     with mono- or polyhydric alcohols, for example with methanol,     ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol,     ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene     glycol, diethylene glycol, triethylene glycol, pentaerythritol,     tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,     3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,     trimethylolpropane,     4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]-octane. -   1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with     mono- or polyhydric alcohols, for example with methanol, ethanol,     octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene     glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol,     diethylene glycol, triethylene glycol, pentaerythritol,     tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide,     3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol,     trimethylolpropane,     4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane. -   1.17. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid,     for example     N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide,     N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamide,     N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide,     N,N′-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]-propionyloxy)ethyl]oxamide     (Naugard XL-1 (RTM), supplied by Uniroyal). -   1.18. Ascorbic acid (vitamin C) -   1.19. Aminic antioxidants, for example     N,N′-di-isopropyl-p-phenylenediamine,     N,N′-di-sec-butyl-p-phenylenediamine,     N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine,     N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine,     N,N′-bis(1-methylheptyl)-p-phenylenediamine,     N,N′-dicyclohexyl-p-phenylenediamine,     N,N′-diphenyl-p-phenylenediamine,     N,N′-bis(2-naphthyl)-p-phenylenediamine,     N-isopropyl-N′-phenyl-p-phenylenediamine,     N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine,     N-(1-methylheptyl)-N′-phenyl-p-phenylenediamine,     N-cyclohexyl-N′-phenyl-p-phenylenediamine,     4-(p-toluenesulfamoyl)diphenylamine,     N,N′-dimethyl-N,N′-di-sec-butyl-p-phenylenediamine, diphenylamine,     N-allyldiphenylamine, 4-isopropoxydiphenylamine,     N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine,     N-phenyl-2-naphthylamine, octylated diphenylamine, for example     p,p′-di-tert-octyldiphenylamine, 4-n-butylaminophenol,     4-butyrylaminophenol, 4-nonanoylaminophenol,     4-dodecanoylaminophenol, 4-octadecanoylaminophenol,     bis(4-methoxyphenyl)amine,     2,6-di-tert-butyl-4-dimethylaminomethylphenol,     2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane,     N,N,N′,N′-tetramethyl-4,4′-diaminodiphenylmethane,     1,2-bis[(2-methylphenyl)amino]-ethane, 1,2-bis(phenylamino)propane,     (o-tolyl)biguanide, bis[4-(1′,3′-dimethylbutyl)phenyl]amine,     tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- and     dialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono-     and dialkylated nonyldiphenylamines, a mixture of mono- and     dialkylated dodecyldiphenylamines, a mixture of mono- and     dialkylated isopropyl/isohexyldiphenylamines, a mixture of mono- and     dialkylated tert-butyldiphenylamines,     2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a     mixture of mono- and dialkylated     tert-butyl/tert-octylphenothiazines, a mixture of mono- and     dialkylated tert-octylphenothiazines, N-allylphenothiazine,     N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene,     N,N-bis(2,2,6,6-tetramethylpiperid-4-yl-hexamethylenediamine,     bis(2,2,6,6-tetramethylpiperid-4-yl)sebacate,     2,2,6,6-tetramethylpiperidin-4-one,     2,2,6,6-tetramethylpiperidin-4-ol. -   2. UV absorbers and light stabilisers -   2.1. 2-(2′-Hydroxyphenyl)benzotriazoles, for example     2-(2′-hydroxy-5′-methylphenyl)benzotriazole,     2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)benzotriazole,     2-(5′-tert-butyl-2′-hydroxyphenyl)benzotriazole,     2-(2′-hydroxy-5′-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole,     2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)-5-chlorobenzotriazole,     2-(3′-tert-butyl-2′-hydroxy-5′-methylphenyl)-5-chlorobenzotriazole,     2-(3′-sec-butyl-5′-tert-butyl-2′-hydroxyphenyl)benzotriazole,     2-(2′-hydroxy-4′-octyloxyphenyl)benzotriazole,     2-(3′,5′-di-tert-amyl-2′-hydroxyphenyl)benzotriazole,     2-(3′,5′-bis(α,α-dimethylbenzyl)-2′-hydroxyphenyl)benzotriazole,     2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazole,     2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)-5-chlorobenzotriazole,     2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)phenyl)-5-chlorobenzotriazole,     2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)phenyl)benzotriazole,     2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)benzotriazole,     2-(3′-tert-butyl-5-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)benzotriazole,     2-(3′-dodecyl-2′-hydroxy-5′-methylphenyl)benzotriazole,     2-(3′-tert-butyl-2′-hydroxy-5′-(2-isooctyloxycarbonylethyl)phenylbenzotriazole,     2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazole-2-ylphenol];     the transesterification product of     2-[3′-tert-butyl-5′-(2-methoxycarbonylethyl)-2′-hydroxyphenyl]-2H-benzotriazole     with polyethylene glycol 300;

where R′=3′-tert-butyl-4′-hydroxy-5′-2H-benzotriazol-2-ylphenyl, 2-[2′-hydroxy-3′-(α,α-dimethylbenzyl)-5′-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole; 2-[2′-hydroxy-3′-(1,1,3,3-tetramethylbutyl)-5′-(α,α-dimethylbenzyl)phenyl]benzotriazole.

-   2.2. 2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy,     4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy,     4,2′,4′-trihydroxy and 2′-hydroxy-4,4′-dimethoxy derivatives. -   2.3. Esters of substituted and unsubstituted benzoic acids, for     example 4-tert-butylphenyl salicylate, phenyl salicylate,     octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butyl     benzoyl)resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl     3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl     3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl     3,5-di-tert-butyl-4-hydroxybenzoate,     2-methyl-4,6-di-tert-butylphenyl     3,5-di-tert-butyl-4-hydroxybenzoate. -   2.4. Acrylates, for example ethyl α-cyano-β,β-diphenylacrylate,     isooctyl α-cyano-β,β-diphenylacrylate, methyl     α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate,     butyl α-cyano-β-methyl-p-methoxycinnamate, methyl     α-carbomethoxy-p-methoxycinnamate,     N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline and neopentyl     tetra(α-cyano-β,β-diphenylacrylate). -   2.5. Nickel compounds, for example nickel complexes of     2,2′-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol], such as the 1:1 or     1:2 complex, with or without additional ligands such as     n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel     dibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g.     the methyl or ethyl ester, of     4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, nickel complexes     of ketoximes, e.g. of 2-hydroxy-4-methylphenylundecylketoxime,     nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or     without additional ligands. -   2.6. Sterically hindered amines, for example     bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate,     bis(2,2,6,6-tetramethyl-4-piperidyl)succinate,     bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate,     bis(1,2,2,6,6-pentamethyl-4-piperidyl)     n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of     1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and     succinic acid, linear or cyclic condensates of     N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and     4-tert-octylamino-2,6-dichloro-1,3,5-triazine,     tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate,     tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate,     1,1′-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone),     4-benzoyl-2,2,6,6-tetramethylpiperidine,     4-stearyloxy-2,2,6,6-tetramethylpiperidine,     bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate,     3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,     bis(1-octyloxy-2,2,6,6-tetramethylpiperid-4-yl)sebacate,     bis(1-octyloxy-2,2,6,6-tetramethylpiperid-4-yl)succinate,     bis-[2,2,6,6-tetramethyl-1-(undecyloxy)piperidin-4-yl] carbonate,     linear or cyclic condensates of     N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylenediamine and     4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of     2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine     and 1,2-bis(3-aminopropylamino)ethane, the condensate of     2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine     and 1,2-bis(3-aminopropyl-amino)ethane,     8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,     3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione,     3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione,     a mixture of 4-hexadecyloxy- and     4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensate of     N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and     4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, a condensate of     1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine     as well as 4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No.     [136504-96-6]); a condensate of 1,6-hexanediamine and     2,4,6-trichloro-1,3,5-triazine as well as N,N-dibutylamine and     4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No. [192268     64-7]); N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide,     N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide,     2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane,     a reaction product of     7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decane     and epichlorohydrin,     1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)ethene,     N,N′-bis-formyl-N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine,     a diester of 4-methoxymethylenemalonic acid with     1,2,2,6,6-pentamethyl-4-hydroxypiperidine,     poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyl)]siloxane,     a reaction product of maleic acid anhydride-α-olefin copolymer with     2,2,6,6-tetramethyl-4-aminopiperidine or     1,2,2,6,6-pentamethyl-4-aminopiperidine, a mixture of oligomeric     compounds which are the formal condensation products of     N,N′-bis-(2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl)-hexane-1,6-diamine     and     2,4-dichloro-6-{n-butyl-(2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl)-amino}-[1,3,5]triazine     end-capped with 2-chloro-4,6-bis-(di-n-butylamino)-[1,3,5]triazine,     a mixture of oligomeric compounds which are the formal condensation     products of     N,N′-bis-(2,2,6,6-tetramethyl-piperidin-4-yl)-hexane-1,6-diamine and     2,4-dichloro-6-{n-butyl-(2,2,6,6-tetramethyl-piperidin-4-yl)-amino}-[1,3,5]triazine     end-capped with 2-chloro-4,6-bis-(di-n-butylamino)-[1,3,5]triazine,     2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)-N-butylamino]-6-(2-hydroxyethyl)amino-1,3,5-triazine,     1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine,     5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl--morpholinone, Sanduvor     (Clariant; CAS Reg. No. 106917-31-1],     5-(2-ethylhexanoyl)-oxymethyl-3,3,5-trimethyl-2-morpholinone, the     reaction product of     2,4-bis-[(1-cyclo-hexyloxy-2,2,6,6-piperidine-4-yl)butylamino]-6-chloro-s-triazine     with N,N′-bis-(3-amino-propyl)ethylenediamine),     1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazine-3-one-4-yl)amino)-s-triazine,     1,3,5-tris(N-cyclohexyl-N-(1,2,2,6,6-pentamethylpiperazine-3-one-4-yl)-amino)-s-triazine. -   2.7. Oxamides, for example 4,4′-dioctyloxyoxanilide,     2,2′-diethoxyoxanilide, 2,2′-dioctyloxy-5,5′-di-tert-butoxanilide,     2,2′-didodecyloxy-5,5′-di-tert-butoxanilide,     2-ethoxy-2′-ethyloxanilide, N,N′-bis(3-dimethylaminopropyl)oxamide,     2-ethoxy-5-tert-butyl-2′-ethoxanilide and its mixture with     2-ethoxy-2′-ethyl-5,4′-di-tert-butoxanilide, mixtures of o- and     p-methoxy-disubstituted oxanilides and mixtures of o- and     p-ethoxy-disubstituted oxanilides. -   2.8. 2-(2-Hydroxyphenyl)-1,3,5-triazines, for example     2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine,     2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,     2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,     2,4-bis(2-hydroxy-4-propyhoxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine,     2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine,     2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,     2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,     2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,     2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine,     2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,     2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine,     2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazine,     2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine,     2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine,     2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine,     2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]-phenyl}-4,6-bis-(2,4-dimethylphenyl)-1,3,5-triazine. -   3. Metal deactivators, for example N,N′-diphenyloxamide,     N-salicylal-N′-salicyloyl hydrazine, N,N′-bis(salicyloyl)hydrazine,     N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine,     3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl     dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl     bisphenylhydrazide, N,N′-diacetyladipoyl dihydrazide,     N,N′-bis(salicyloyl)oxalyldihydrazide,     N,N′-bis(salicyloyl)thiopropionyl dihydrazide. -   4. Phosphites and phosphonites, for example triphenyl phosphite,     diphenylalkyl phosphites, phenyldialkyl phosphites,     tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl     phosphite, distearylpentaerythritol di phosphite,     tris(2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol     diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol     diphosphite, bis(2,4-di-cumylphenyl)pentaerythritol diphosphite,     bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite,     diisodecyloxypentaerythritol diphosphite,     bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite,     bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite,     tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)     4,4′-biphenylene diphosphonite,     6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin,     bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite,     bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite,     6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin,     2,2′,2″-nitrilo-[triethyltris(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite],     2-ethylhexyl-(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite,     5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphirane.

The following phosphites are especially preferred:

Tris(2,4-di-tert-butylphenyl) phosphite (Irgafos 168, RTM BASF), tris(nonylphenyl) phosphite,

-   5. Hydroxylamines and amine N-oxides, for example     N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine,     N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine,     N,N-ditetradecylhydroxylamine, N,N-dihexadecylhydroxylamine,     N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine,     N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine     derived from hydrogenated tallow amine or N,N-bis-(hydrogenated     rape-oil alkyl)-N-methyl-amine N-oxide. -   6. Nitrones, for example N-benzyl-alpha-phenylnitrone,     N-ethyl-alpha-methylnitrone, N-octyl-alpha-heptylnitrone,     N-lauryl-alpha-undecylnitrone, N-tetradecyl-alpha-tridecylnitrone,     N-hexadecyl-alpha-pentadecylnitrone,     N-octadecyl-alpha-heptadecylnitrone,     N-hexadecyl-alpha-heptadecylnitrone,     N-ocatadecyl-alpha-pentadecylnitrone,     N-heptadecyl-alpha-heptadecylnitrone,     N-octadecyl-alpha-hexadecylnitrone, nitrone derived from     N,N-dialkylhydroxylamine derived from hydrogenated tallow amine. -   7. Thiosynergists, for example dilauryl thiodipropionate, dimistryl     thiodipropionate, distearyl thiodipropionate and pentaerythritol     tetrakis-[3-(n-lauryl)-propionic acid ester]. -   8. Peroxide scavengers, for example esters of a-thiodipropionic     acid, for example the lauryl, stearyl, myristyl or tridecyl esters,     mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole,     zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol     tetrakis(β-dodecylmercapto)propionate. -   9. Polyamide stabilizers, for example copper salts in combination     with iodides and/or phosphorus compounds and salts of divalent     manganese. -   10. Acid scavengers, for example melamine, polyvinylpyrrolidone,     dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine     derivatives, amines, polyamides, polyurethanes, alkali metal salts     and alkaline earth metal salts of higher fatty acids, for example     calcium stearate, zinc stearate, magnesium behenate, magnesium     stearate, sodium ricinoleate and potassium palmitate, antimony     pyrocatecholate and zinc pyrocatecholate. -   11. Benzofuranones and indolinones, for example those disclosed in     U.S. Pat. Nos. 4,325,863; 4,338,244; 5,175,312; 5,216,052;     5,252,643; DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 or     EP-A-0591102 or     3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-one,     5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one,     3,3′-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]-phenyl)benzofuran-2-one],     5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one,     3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,     3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one,     3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one,     3-(2,3-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one and     3-(2-acetoxy-4-(1,1,3,3-tetramethyl-butyl)-phenyl)-5-(1,1,3,3-tetramethyl-butyl)benzofuran-2-one. -   12. Nucleating agents, for example inorganic substances, such as     talcum, metal oxides, such as titanium dioxide or magnesium oxide,     phosphates, carbonates or sulfates of, preferably, alkaline earth     metals; organic compounds, such as mono- or polycarboxylic acids and     the salts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid,     diphenylacetic acid, sodium succinate or sodium benzoate; polymeric     compounds, such as ionic copolymers (ionomers), Irgaclear XT 386     (RTM BASF), 1,3:2,4-bis(3′,4′-dimethylbenzylidene)-sorbitol,     1,3:2,4-di(paramethyldibenzylidene)-sorbitol, and     1,3:2,4-di(benzylidene)sorbitol. -   13. Fillers and reinforcing agents, for example calcium carbonate,     silicates, glass fibres, glass beads, asbestos, talc, kaolin,     bentonite, mica, hydrotalcite, barium sulfate, metal oxides and     hydroxides, carbon black, graphite, wood flour and flours or fibers     of other natural products, synthetic fibers. -   14. Other additives, for example plasticisers, lubricants, rheology     additives, catalysts, flow-control agents, optical brighteners,     flameproofing agents, antistatic agents and blowing agents.

Preferred is a composition, which comprises a component a), a component b) and as component c) a further additive.

Preferred is a composition, wherein the weight ratio of component b) to component c) is from 10:1 to 1:30, in particular from 4:1 to 1:20, especially from 2:1 to 1:10, and wherein the overall amount of component b) and component c) is below 50% by weight of component a).

Preferred is a composition, which comprises as component c) a further additive selected from the group consisting of an antioxidant, an UV absorber, a hindered amine light stabilizer, a nickel compound, a metal deactivator, a phosphite or phosphonite, a hydroxylamine or amine N-oxide, a thiosynergist, a peroxide scavenger, a nucleating agent and a filler or reinforcing agent.

Preferred is a composition, which comprises as component c) a further additive selected from the group consisting of a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant and an aminic antioxidant.

Preferred is a composition, which comprises as component c) a phenolic antioxidant.

Preferred is a composition, which comprises as component c) a phenolic antioxidant, which is an ester of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid.

Optionally, a composition comprising a component a), a component b) and a component c) contains as component d) a second further additive.

Preferred is a composition, which comprises a component a), a component b), as component c) a further additive and as component d) a second further additive.

Preferred is a composition, wherein the weight ratio of component b) to component d) is from 10:1 to 1:30, in particular from 4:1 to 1:20, especially from 2:1 to 1:10, and wherein the overall amount of component b), component c) and component d) is below 50% by weight of component a).

Preferred is a composition, which comprises a component a), a component b), as component c) a further additive, which is selected from the group consisting of a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant and an aminic antioxidant, and as component d) a second further additive.

Preferred is a composition, which comprises a component a), a component b), a component c) and a component d), wherein component c) and component d) are independently from each other a phosphite or phosphonite, an acid scavenger, a phenolic antioxidant or an aminic antioxidant.

Preferred is a composition, which comprises a component a), a component b), as component c) a phenolic antioxidant and as component d) a phosphite or phosphonite.

Preferred is a composition, which comprises a component a), a component b), as component c) a phenolic antioxidant and as component d) an aminic antioxidant.

The above described preferences for a compound of formula I and an organic material susceptible to oxidative, thermal or light-induced degradation apply also to the further embodiments of the invention. This applies also to the optional further additive and the optional second further additive.

A further embodiment of the invention relates to a process for protection of an organic material susceptible to oxidative, thermal or light-induced degradation, i.e. component a), which comprises the step of incorporation into or application onto an organic material, a compound of formula I, i.e. component b).

The incorporation or application of component b) can be carried out in a processing apparatus, in particular a heatable container equipped with a stirrer, which can preferably be closed. A heatable container equipped with a stirrer is for example a kneader, extruder, mixer or stirred vessel. Specific examples thereof are a single-screw extruder, contrarotating and corotating twin-screw extruder, planetary-gear extruder, ring extruder or co-kneader. It is also possible to use a processing apparatus, which contains at least one gas removal compartment to which a vacuum can be applied and/or which can be set under an atmosphere, wherein the oxygen content is low or oxygen is absent. Component b) can be added directly into the processing apparatus.

Component b) can be incorporated or applied to at any stage of processing of component a), in particular prior to or during a shaping operation of component a) in the processing apparatus.

Component b) can be incorporated or applied in the form of a dry powder, in the form of a melt, in encapsulated form such as encapsulation in a wax or polymer or in the form of a wet mixture such as a solution, dispersion or suspension for example in an inert solvent, water or oil. A dispersing or suspension agent can be present in the case of a wet mixture of component b).

Component b) can also be incorporated or applied by spraying onto component a).

In case that component a) is a polymer, a further possibility for incorporation or application of component b) to component a) is addition before, during or directly after the polymerization of the corresponding starting materials, e.g. monomers, of component a). For example, spraying during the deactivation of the polymerization catalysts is particularly advantageous. If crosslinking takes place during formation of component a), incorporation or application prior to crosslinking is preferred.

In case that component a) is a polymer, the process of incorporation or application is preferably a moulding process, in particular an injection-moulding, blow-moulding, compression-moulding, roto-moulding, slush-moulding or extrusion-moulding.

Preferred is a process, wherein the incorporation or application takes place at a temperature in the range from 150 to 340° C., in particular from 180° C. to 330° C., especially from 190° C. to 320° C.

Preferred is a process, wherein component b) is incorporated or applied to in an extruder during processing of component a).

In case of a further additive, i.e. component c) or components c) and d), component b) and the further additive can be incorporated into or applied onto component a) individually or mixed with one another. If desired, the individual components can be mixed with one another before incorporation into component a) for example by dry blending, compaction, melting, encapsulation by a wax or polymer or as wet mixture in the form of solutions, dispersions or suspensions for example in an inert solvent, water or oil.

Component b) and a further additive can also be added to component a) in the form of a masterbatch (‘concentrate’), which contains the component b), a further additive and a masterbatch polymer. The component b) and a further additive are incorporated into the masterbatch in a concentration of, for example, from 1% to 40% and preferably 2% to 20% by weight of the masterbatch. The masterbatch polymer content is the difference towards 100% by weight of the masterbatch. The masterbatch polymer must not be necessarily the same as polymer as component a) in case the latter one is a polymer.

A further embodiment of the invention relates to an additive composition, which comprises

-   b) a compound of formula I, and -   c) a further additive selected from a group consisting of a     phosphite or phosphonite, an acid scavenger, a phenolic antioxidant     or an aminic antioxidant.

Preferred is a composition, wherein the weight ratio of component b) to component c) is from 10:1 to 1:30, in particular from 4:1 to 1:20, especially from 2:1 to 1:10.

Preferred is an additive composition, which comprises as component d) a second further additive.

Preferred is an additive composition, which comprises

-   b) a compound of formula I, -   c) a further additive selected from a group consisting of a     phosphite or phosphonite, an acid scavenger, a phenolic antioxidant     or an aminic antioxidant, and -   d) a second further additive selected from a group consisting of a     phosphite or phosphonite, an acid scavenger, a phenolic antioxidant     or an aminic antioxidant.

Preferred is a composition, wherein the weight ratio of component b) to component c) is from 10:1 to 1:30, in particular from 4:1 to 1:20, especially from 2:1 to 1:10, and wherein the weight ratio of component b) to component d) is from 10:1 to 1:30, in particular from 4:1 to 1:20, especially from 2:1 to 1:10.

A further embodiment of the invention relates to an article, which is made from a composition comprising

-   a) an organic material susceptible to oxidative, thermal or     light-induced degradation, which is a polymer, and -   b) a compound of formula I.

The composition can be advantageously used for the preparation of various shaped articles. Examples for such an article are:

-   I-1) Floating devices, marine applications, pontoons, buoys, plastic     lumber for decks, piers, boats, kayaks, oars, and beach     reinforcements. -   I-2) Automotive applications, in particular bumpers, dashboards,     battery, rear and front linings, moldings parts under the hood, hat     shelf, trunk linings, interior linings, air bag covers, electronic     moldings for fittings (lights), panes for dashboards, headlamp     glass, instrument panel, exterior linings, upholstery, automotive     lights, head lights, parking lights, rear lights, stop lights,     interior and exterior trims; door panels; gas tank; glazing front     side; rear windows; seat backing, exterior panels, wire insulation,     profile extrusion for sealing, cladding, pillar covers, chassis     parts, exhaust systems, fuel filter/filler, fuel pumps, fuel tank,     body side mouldings, convertible tops, exterior mirrors, exterior     trim, fasteners/fixings, front end module, glass, hinges, lock     systems, luggage/roof racks, pressed/stamped parts, seals, side     impact protection, sound deadener/insulator and sunroof. -   I-3) Road traffic devices, in particular sign postings, posts for     road marking, car accessories, warning triangles, medical cases,     helmets, tires. -   I-4) Devices for plane, railway, motor car (car, motorbike, trucks)     including furnishings. -   I-5) Devices for space applications, in particular rockets and     satellites, e.g. reentry shields. -   I-6) Devices for architecture and design, mining applications,     acoustic quietized systems, street refuges, and shelters. -   II-1) Appliances, cases and coverings in general and     electric/electronic devices (personal computer, telephone, portable     phone, printer, television-sets, audio and video devices), flower     pots, satellite TV bowl, and panel devices. -   II-2) Jacketing for other materials such as steel or textiles. -   II-3) Devices for the electronic industry, in particular insulation     for plugs, especially computer plugs, cases for electric and     electronic parts, printed boards, and materials for electronic data     storage such as chips, check cards or credit cards. -   II-4) Electric appliances, in particular washing machines, tumblers,     ovens (microwave oven), dish-washers, mixers, and irons. -   II-5) Covers for lights (e.g. street-lights, lamp-shades). -   II-6) Applications in wire and cable (semi-conductor, insulation and     cable-jacketing). -   II-7) Foils for condensers, refrigerators, heating devices, air     conditioners, encapsulating of electronics, semi-conductors, coffee     machines, and vacuum cleaners. -   III-1) Technical articles such as cogwheel (gear), slide fittings,     spacers, screws, bolts, handles, and knobs. -   III-2) Rotor blades, ventilators and windmill vanes, solar devices,     swimming pools, swimming pool covers, pool liners, pond liners,     closets, wardrobes, dividing walls, slat walls, folding walls,     roofs, shutters (e.g. roller shutters), fittings, connections     between pipes, sleeves, and conveyor belts. -   III-3) Sanitary articles, in particular shower cubicles, lavatory     seats, covers, and sinks. -   III-4) Hygienic articles, in particular diapers (babies, adult     incontinence), feminine hygiene articles, shower curtains, brushes,     mats, tubs, mobile toilets, tooth brushes, and bed pans. -   III-5) Pipes (cross-linked or not) for water, waste water and     chemicals, pipes for wire and cable protection, pipes for gas, oil     and sewage, guttering, down pipes, and drainage systems. -   III-6) Profiles of any geometry (window panes) and siding. -   III-7) Glass substitutes, in particular extruded or co-extruded     plates, glazing for buildings (monolithic, twin or multiwall),     aircraft, schools, extruded sheets, window film for architectural     glazing, train, transportation, sanitary articles, and greenhouse. -   III-8) Plates (walls, cutting board), extrusion-coating     (photographic paper, tetrapack and pipe coating), silos, wood     substitute, plastic lumber, wood composites, walls, surfaces,     furniture, decorative foil, floor coverings (interior and exterior     applications), flooring, duck boards, and tiles. -   III-9) Intake and outlet manifolds. -   III-10) Cement-, concrete-, composite-applications and covers,     siding and cladding, hand rails, banisters, kitchen work tops,     roofing, roofing sheets, tiles, and tarpaulins. -   IV-1) Plates (walls and cutting board), trays, artificial grass,     astroturf, artificial covering for stadium rings (athletics),     artificial floor for stadium rings (athletics), and tapes. -   IV-2) Woven fabrics continuous and staple, fibers (carpets/hygienic     articles/geotextiles/monofilaments; filters; wipes/curtains     (shades)/medical applications), bulk fibers (applications such as     gown/protection clothes), nets, ropes, cables, strings, cords,     threads, safety seat-belts, clothes, underwear, gloves; boots;     rubber boots, intimate apparel, garments, swimwear, sportswear,     umbrellas (parasol, sunshade), parachutes, paraglides, sails,     “balloon-silk”, camping articles, tents, airbeds, sun beds, bulk     bags, and bags. Non-woven fabrics such as medical fabrics and     related apparel, industrial apparel, outdoor fabrics, in-home     furnishing and construction fabrics. -   IV-3) Membranes, insulation, covers and seals for roofs, tunnels,     dumps, ponds, dumps, walls roofing membranes, geomembranes, swimming     pools, curtains (shades)/sun-shields, awnings, canopies, wallpaper,     food packing and wrapping (flexible and solid), medical packaging     (flexible & solid), airbags/safety belts, arm- and head rests,     carpets, centre console, dashboard, cockpits, door, overhead console     module, door trim, headliners, interior lighting, interior mirrors,     parcel shelf, rear luggage cover, seats, steering column, steering     wheel, textiles, and trunk trim. -   V) Films (packaging, dump, laminating, agriculture and horticulture,     greenhouse, mulch, tunnel, silage), bale wrap, swimming pools, waste     bags, wallpaper, stretch film, raffia, desalination film, batteries,     and connectors. -   VI-1) Food packing and wrapping (flexible and solid), bottles. -   VI-2) Storage systems such as boxes (crates), luggage, chest,     household boxes, pallets, shelves, tracks, screw boxes, packs, and     cans. -   VI-3) Cartridges, syringes, medical applications, containers for any     transportation, waste baskets and waste bins, waste bags, bins, dust     bins, bin liners, wheely bins, container in general, tanks for     water/used water/chemistry/gas/oil/gasoline/diesel; tank liners,     boxes, crates, battery cases, troughs, medical devices such as     piston, ophthalmic applications, diagnostic devices, and packing for     pharmaceuticals blister. -   VII-1) Extrusion coating (photo paper, tetrapack, pipe coating),     household articles of any kind (e.g. appliances, thermos     bottle/clothes hanger), fastening systems such as plugs, wire and     cable clamps, zippers, closures, locks, and snap-closures. -   VII-2) Support devices, articles for the leisure time such as sports     and fitness devices, gymnastics mats, ski-boots, inline-skates,     skis, big foot, athletic surfaces (e.g. tennis grounds); screw tops,     tops and stoppers for bottles, and cans. -   VII-3) Furniture in general, foamed articles (cushions, impact     absorbers), foams, sponges, dish clothes, mats, garden chairs,     stadium seats, tables, couches, toys, building kits     (boards/figures/balls), playhouses, slides, and play vehicles. -   VII-4) Materials for optical and magnetic data storage. -   VII-5) Kitchen ware (eating, drinking, cooking, storing). -   VII-6) Boxes for CD's, cassettes and video tapes; DVD electronic     articles, office supplies of any kind (ball-point pens, stamps and     ink-pads, mouse, shelves, tracks), bottles of any volume and content     (drinks, detergents, cosmetics including perfumes), and adhesive     tapes. -   VII-7) Footwear (shoes/shoe-soles), insoles, spats, adhesives,     structural adhesives, food boxes (fruit, vegetables, meat, fish),     synthetic paper, labels for bottles, couches, artificial joints     (human), printing plates (flexographic), printed circuit boards, and     display technologies. -   VII-8) Devices of filled polymers (talc, chalk, china clay (kaolin),     wollastonite, pigments, carbon black, TiO₂, mica, nanocomposites,     dolomite, silicates, glass, asbestos).

Preferred is an article, which is a film, pipe, profile, bottle, tank, container or fiber.

Preferred is an article, which is moulded. In particular, the moulding is effected by injection, blow, compression, roto-moulding, slush-moulding or extrusion.

A further embodiment to the invention relates to the use of a compound of formula I, i.e. component b), for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation, i.e. component a), against degradation by oxidation, heat or light.

Preferred is the use of component b) for stabilizing a polyurethane foam against scorching.

Processing of a component a) is characterized as short-term exposure of the component a) to heat, for example to a temperature in the range of 150° C. to 340° C., during the time of processing of component a). The time of processing is short in comparison to for example the possible time of usage. Usage takes typically place at a temperature, for example 0° C. to 50° C., which is below the temperature during processing.

Preferred is the use of component b) for stabilizing a component a) against oxidative or thermal degradation during processing.

Compounds of formula I are partly new and partly known. Several synthetic routes to known compounds of formula I are described in literature.

A further embodiment of the invention relates to a compound of formula I

wherein

-   when n is 1 -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃) or —SO₂-phenyl; -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or     piperazine-N,N′-biscarbonyl; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl),     3-ethyl-3-azapentane-1,5,2′-tri-(oxycarbonyl),     1,4,7-triazaheptane-1,4,7-tricarbonyl,     1,4,8-triazaoctane-1,4,8-tricarbonyl or     1,5,9-triazanonane-1,5,9-tricarbonyl; -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl),     1,4,7,10-tetraazadecane-1,4,7,10-tetracarbonyl,     1,4,8,11-tetraazaundecane-1,4,8,11-tetracarbonyl or     1,5,8,12-tetraazadodecane-1,5,8,12-tetracarbonyl; -   n is 1, 2, 3 or 4; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,     C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to     three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or     tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which     is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which     is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is     interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,     which is substituted by a hydroxyl group,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     5-, 6- or 7-membered saturated heterocycle; -   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl, C₄-C₈-cycloalkyl     -C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,     C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms,     hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or 1-ethyl     -2,2,6,6-tetramethylpiperidine-4,2′-diyl; and -   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,     C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms,     3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

Preferred is a compound of formula I, wherein

-   when n is 1 -   A is —C(═O)—OR′1 or —C(═O)—N(R′₂)(R′₃); -   when n is 2 -   A is —C(═O)—O—Z₁—O—C(═O)—, —C(═O)—N(R″₁)—Z₂—N(R″₂)—C(═O)— or     piperazine-N,N′-biscarbonyl; -   when n is 3 -   A is C₃-C₁₂-alkane-tri-(oxycarbonyl); -   when n is 4 -   A is C₄-C₁₆-alkane-tetra-(oxycarbonyl); -   n is 1, 2, 3 or 4; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,     C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to     three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or     tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which     is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which     is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is     interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₆-alkyl,     which is substituted by a hydroxyl group,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     5-, 6- or 7-membered saturated heterocycle; -   R″₁ and R″₂ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl; -   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,     C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms,     hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl or     1-ethy-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and -   Z₂ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene, C₆-C₁₄-arylene,     C₄-C₈-cycloalkane-bis(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₄-C₁₂-alkylene, which is     interrupted by one or more oxygen atoms,     3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl or     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diyl.

A further embodiment of the invention relates to a synthesis method for a compound of formula I

wherein

-   n is 1; -   A is —C(═O)—OR′₁, —C(═O)—N(R′₂)(R′₃); -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; -   R′₁ is H, C₁-C₂₂-alkyl, C₂-C₁₈-alkenyl, C₃-C₁₂-alkine-yl,     C₄-C₈-cycloalkyl, which is unsubstituted or substituted by one to     three C₁-C₄-alkyl, C₄-C₈-cycloalkyl-C₁-C₄-alkyl, bicyclic or     tricyclic C₅-C₂₀-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₁₂-alkyl, which     is substituted by one or more hydroxyl groups, C₄-C₁₂-alkyl, which     is interrupted by one or more oxygen atoms, C₄-C₁₈-alkyl, which is     interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; -   R′₂ and R′₃ are independently from each other H, C₁-C₂₂-alkyl,     C₂-C₁₈-alkenyl, C₄-C₈-cycloalkyl, which is unsubstituted or     substituted by one to three C₁-C₄-alkyl, C₆-C₁₀-aryl,     C₄-C₈-cycloalkyl-C₁-C₄-alkyl, C₆-C₁₄-aryl-C₁-C₄-alkyl, C₂-C₈-alkyl,     which is substituted by one hydroxyl group,     2,2,6,6-tetramethylpiperidine-4-yl,     1-(C₁-C₈-alkyl)-2,2,6,6-tetramethylpiperidin-4-yl or     1-(C₁-C₈-alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′₂ and R′₃     form together with the nitrogen atom to which they are attached a     5-, 6- or 7-membered saturated heterocycle;

which comprises the step of reacting a compound of formula II

wherein

-   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ have the meaning as     indicated above; with a compound of formula III

wherein

-   R_(e) is C₁-C₈-alkyl; -   Y is OR′₁ or N(R′₂)(R′₃); and -   R′₁, R′₂ and R′₃ have the meaning as indicated above;     in the presence of an organic or inorganic base and a solvent.

Preferably, R_(e) is C₁-C₄-alkyl, in particular methyl or ethyl.

Preferably, the organic base is sodium methanolate or sodium ethanolate.

Preferably, the solvent is methanol or ethanol, in particular methanol.

Preferably, the temperature during the synthesis is in the range of 0° C. to 240° C.

A further embodiment of the invention relates to a synthesis method for a compound of formula I

wherein

-   n is 2; -   A is —C(═O)—O—Z₁—O—C(═O)—; -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ are independently from     each other H, C₁-C₈-alkyl, C₄-C₈-cycloalkyl, phenyl, C₁-C₄-alkoxy or     halogen; and -   Z₁ is C₂-C₁₂-alkylene, C₄-C₈-cycloalkylene,     C₄-C₈-cycloalkane-bis-(C₁-C₄-alkylene),     C₆-C₁₄-arene-bis-(C₁-C₄-alkylene), C₃-C₆-alkylene, which is     substituted by one or more hydroxyl groups, C₄-C₁₂-alkylene, which     is interrupted by one or more oxygen atoms,     hexahydro-furo[3,2-b]furane-3,6-diyl, C₄-C₈-alkylene, which is     interrupted by a sulfur atom, 3-(C₁-C₈-alkyl)-3-azapentane-1,5-diyl,     4-(C₁-C₈-alkyl)-4-azaheptane-1,7-diylor     1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl;

which comprises the step of reacting a compound of formula Ia

wherein

-   R_(ee) is C₁-C₈-alkyl; and -   R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ and R₁₀ have the meaning as     indicated above;

with a compound of formula V HO—Z₁—OH   (V) wherein Z₁ has the meaning as indicated above;

in the presence of a solvent.

Preferably, the temperature during the synthesis is in the range of 70° C. to 240° C.

Preferably, R_(e) is C₁-C₄-alkyl, in particular methyl or ethyl.

Preferably, the solvent has a boiling point above the boiling point of R_(ee)—OH. Preferably, the solvent is free of a hydroxyl group. For example, the solvent is toluene, xylene or dichlorobenzene.

Preferably, the synthesis is conducted under vacuum.

Preferably, a transesterification catalyst is added.

The following examples illustrate further the invention without limiting it.

EXAMPLE 1 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid methyl ester (201)

45 g benzoin (=2-hydroxy-1,2-bis-phenyl-ethanone; 212 mmol) and 70 g dimethyl malonate (530 mmol) are dissolved under reflux in 75 mL methanol. 22.9 g sodium methoxide (424 mmol) is dissolved in 1250 mL methanol and added. The mixture is stirred at 40° for 1 h and then acidified with diluted aqueous hydrochloric acid to pH 3-4. The precipitate is filtered off, washed with water and afterwards with methanol and dried in vacuo. 50.8 g of compound (201) are obtained (81%); mp. 113-115°.

EXAMPLE 2 4,5-Bis-(4-methoxy-phenyl)-2-oxo-2,5-dihydro-furan-3-carboxylic acid methyl ester (202)

10 g anisoin (=2-hydroxy-1,2-bis-(4-methoxy-phenyl)-ethanone; 36.7 mmol) and 12.13 g dimethyl malonate (91.8 mmol) are dissloved in 70 mL methanol under reflux. 1.68 g sodium (73.4 mmol) is dissolved in 70 mL methanol and added. The mixture is refluxed for 18 h, then cooled to 25° and acidified with diluted aqueous hydrochloric acid. The resulting mixture is extracted with ethyl acetate/toluene. The organic phases are washed with water, dried over magnesium sulfate, and evaporated to dryness. Recrystallization from methanol yields 5.61 g of compound (202) (41%); mp. 107-109°.

EXAMPLE 3 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid amide (203)

10 g benzoin (47 mmol) and 11 g methyl malonamate (94 mmol) are dissolved in 100 mL methanol at reflux. 5.07 g sodium methoxide (94 mmol) is dissolved in 40 mL methanol and added. The mixture is refluxed for 1 h. The resulting suspension is acidified at 25° with diluted aqueous hydrochloric acid to pH 3-4 and the precipitate is filtered off, dried and recrystallized from toluene. 10.1 g of compound (203) is obtained (77%); mp. 125-127°.

EXAMPLE 4 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid octylamide (204)

1 g benzoin (4.7 mmol) and 1.6 g of compound (401) (7 mmol) are dissolved in 5 mL methanol. 0.63 g of sodium methoxide (9.4 mmol) in 5 mL methanol is added and the mixture is refluxed for 2 h. The mixture is acidified with diluted aqueous hydrochloric acid to pH 3-4 and extracted twice with ethyl acetate. The organic phases are washed with water, dried over sodium sulfate and evaporated to dryness. 1.25 g of compound (204) is obtained as vicous oil (68%).

EXAMPLE 5 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid cyclohexylamide (205)

In analogy to example 4, benzoin and compound (402) are reacted and compound (205) is obtained (49%); mp. 151-153° C.

EXAMPLE 6 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid (1,1,3,3-tetra-methyl-butyl)-amide (206)

In analogy to example 4, benzoin and compound (403) are reacted and compound (206) is obtained (64%); mp. 110-111° C.

EXAMPLE 7 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid benzylamide (207)

In analogy to example 4, benzoin and compound (404) are reacted and compound (207) is obtained (54%); mp. 173-175° C.

EXAMPLE 8 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid (2,2,6,6-tetra-methyl-1-propoxy-piperidin-4-yl)-amide (208)

In analogy to example 4, benzoin and compound (405) are reacted and compound (208) is obtained (99%) as waxy solid; mp. 79-85° C.

EXAMPLE 9 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid dibutylamide (209)

7.4 g benzoin (35 mmol) and 12 g of compound (406) (52 mmol) are dissolved in 80 mL methanol at reflux. 3.78 g sodium methoxide (70 mmol) is dissolved in 40 mL methanol and added. The reaction mixture is refluxed for 2.5 h. Then, the mixture is acidified with diluted aqueous hydrochloric acid to pH 3-4 and extracted with diethyl ether. The organic phase is separated, washed with water, dried over sodium sulfate, and evaporated in vacuo. 13.6 g of compound (209) is obtained (99%) as a slightly yellow liquid; MS (liquid chromatography/mass spectroscopy atmospheric pressure chemical ionisation (positive mode) (=LC/MS APCI (pos. mode)): 392 ([MH]⁺).

EXAMPLE 10 3-(Morpholine-4-carbonyl)-4,5-diphenyl-5H-furan-2-one (210)

In analogy to example 9, benzoin and compound (407) are reacted and compound (210) is obtained (92%); mp. 204-206° C.

EXAMPLE 11 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid phenylamide (211)

In analogy to example 9, benzoin and compound (408) are reacted and compound (211) is obtained (58%); mp. 148-150° C.

EXAMPLE 12 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid ethyl ester (212)

5 g of compound (201) (17 mmol) is dissolved in 50 mL ethanol and heated to reflux with a oilbath temperatue of 100° C. A mixture of ethanol and methanol is distilled off. Ethanol is replaced regularly under these distillation conditions. After 8 h of distilling, the turnover is complete and the solution is evaporated in vacuo. 4.77 g of compound (212) is obtained (91%) as a viscous oil.

EXAMPLE 13 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid propyl ester (213)

In analogy to example 12, compound (201) and 1-propanol are reacted and compound (213) is obtained (98%) as a liquid.

EXAMPLE 14 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid pentyl ester (214)

In analogy to example 12, compound (201) and 1-pentanol are reacted and compound (214) is obtained (83%) as liquid.

EXAMPLE 15 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid 1-methoxy-2,2,6,6-tetramethyl-piperidin-4-yl ester (215)

In analogy to example 12 and with tetralin employed as co-solvent, compound (201) and 1-methoxy-2,2,6,6-tetramethyl-piperidin-4-ol are reacted and compound (215) is obtained (37%); mp. 143-146° C.

EXAMPLE 16 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid cyclohexyl ester (216)

In analogy to example 12, compound (201) and cyclohexanol are reacted and compound (216) is obtained (82%); mp. 139-142° C.

EXAMPLE 17 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid benzyl ester (217)

In analogy to example 12, compound (201) and benzyl alcohol are reacted and compound (217) is obtained (73%); mp. 111-114° C.

EXAMPLE 18 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid isopropyl ester (218)

In analogy to example 12, compound (201) and isopropanol are reacted and compound (218) is obtained (85%); mp. 120-122° C.

EXAMPLE 19 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid tert-butyl ester (219)

In analogy to example 12, compound (201) and 2-methyl-2-propanol are reacted and compound (219) is obtained (75%); mp. 109-111° C.

EXAMPLE 20 Bis-(2-oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid) cyclohexane-1,4-diyldiester (220)

50 g of compound (201) (170 mmol) is melted at 140°. 10 g cyclohexan-1,4-diol (mixture of cis- and trans-isomer, 87 mmol) is added and followed by addition of 20 mL o-dichlorobenzene. The resulting methanol is distilled off at oil bath temperature of 190°. After 6 h the mixture is cooled to room temperature and 50 mL toluene is added. The precipitate is filtered off, washed with toluene, then hexane, and dried in vacuo. 18.61 g of compound (220) as a mixture of isomers is obtained (33%); mp. 237-240° C.

EXAMPLE 21 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carboxylic acid (221)

15 g of compound (219) (44 mmol) is stirred into 100 mL of sulfuric acid (96%) at 25°. After 1 h, the solution is added dropwise to a mixture of ice-water and dichloromethane under stirring. The organic phases are washed with water, then brine, dried over sodium sulfate, and evaporated to dryness. Recrystallization from chloroform yields 5.77 g of compound (221) (46%); mp. 116-117°.

EXAMPLE 22 2-Oxo-4,5-diphenyl-2,5-dihydro-furan-3-carbonitrile (222)

Compound (222) is prepared according to J. A. McRae and A. L. Kuehner, Journal of the American Chemical Society, 1930, 52, 3377-3382.

EXAMPLE 23 4,5-Bis-(4-methoxy-phenyl)-2-oxo-2,5-dihydro-furan-3-carbonitrile (223)

Compound (223) is prepared in analogy to compound (222).

EXAMPLE 24 4,5-Diphenyl-5H-furan-2-one (224)

Compound (224) is a known compound.

10 g benzoin (47 mmol) and 37.6 g dimethyl malonate (235 mmol) are heated to 170° C. for 2 h. After cooling to room temperature, the reaction mass is triturated with hexane, the precipitate is filtered off and dried in vacuum. 6.7 g of compound (224) is obtained (60.5%) as white crystals; mp. 147-149° C.

EXAMPLE 25 3-Benzenesulfonyl-4,5-diphenyl-5H-furan-2-one (225)

In analogy to example 2, 2.92 g benzoin (13 mmol) and 5.0 g phenylsulfonyl acetic acid methyl ester (20 mmol) are reacted. 4.02 g of compound (225) is obtained (76%) as yellow oil; MS (LC/MS APCI (pos. mode)): 377 ([MH]⁺).

EXAMPLE 26 3,4,5-Triphenyl-5H-furan-2-one (226)

Compound (226) is a known compound.

40 g benzoin (=2-hydroxy-1,2-bis-phenyl-ethanone; 188 mmol) and 84.9 g methyl-phenyl acetate (565 mmol) are dissolved under reflux in 200 mL methanol. 30.5 g sodium methoxide (565 mmol) is dissolved in 100 mL methanol and added. The mixture is stirred at 65° C. for 15 h and then acidified with diluted aqueous hydrochloric acid to pH 3-4. The precipitate is filtered off, washed with water and afterwards with methanol and dried in vacuo. 44.4 g of compound (226) are obtained, which are recrystallized from ethyl acetate/hexane to obtain 29.9 g (51%) of compound (226) as white crystals; mp. 120-122° C., MS (LC/MS APCI (pos. mode)): 313 ([MH]⁺).

EXAMPLE 27 N-Octyl-malonamic acid methyl ester (401)

13.2 g dimethyl malonate (100 mmol) and 6.45 g octylamine (50 mmol) are heated to 125° C. and resulting methanol is distilled off. After 2.5 h at 125°, the reaction mixture is cooled to room temperature, the side product (bisamide) is precipitated with methanol and removed by filtration. The filtrate is concentrated in vacuo. 7.41 g of compound (401) is obtained (65%) as a liquid; pure by ¹H-NMR.

EXAMPLE 28 N-Cyclohexyl-malonamic acid methyl ester (402)

In analogy to example 27, compound (402) is obtained (64%); mp. 77-78° C.

EXAMPLE 29 N-(1,1,3,3-Tetramethyl-butyl)-malonamic acid methyl ester (403)

In analogy to example 27, compound (403) is obtained (97%); mp. 74-75° C.

EXAMPLE 30 N-Benzyl-malonamic acid methyl ester (404)

In analogy to example 27, compound (404) is obtained (63%); mp. 51-54° C.

EXAMPLE 31 N-(2,2,6,6-Tetramethyl-1-propoxy-piperidin-4-yl)-malonamic acid methyl ester (405)

In analogy to example 27, compound (405) is obtained (55%) as semi-crystalline/waxy material.

EXAMPLE 32 N,N-Dibutyl-malonamic acid methyl ester (406)

10 g methyl malonyl monochloride (=chlorocarbonyl-acetic acid methyl ester; 73 mmol) and 20.8 g dibutylamine (161 mmol, in excess) are reacted in diethylether at 0° C. Compound (406) is obtained (78%) as yellow, viscous oil.

EXAMPLE 33 3-Morpholin-4-yl-3-oxo-propionic acid methyl ester (407)

In analogy to example 32, compound (407) is obtained (69.5%) as orange, viscous oil.

EXAMPLE 34 N-Phenyl-malonamic acid methyl ester (408)

In analogy to example 32, compound (408) is obtained (89.8%) as white crystals.

EXAMPLE 35 Stabilization of Polyol

The oxidation resistance of polyol is determined by differential scanning calorimetry (DSC). A sample is heated starting at 50° C. with a heating rate of 5° C./min under oxygen until 200° C. are reached. The appearance of an exothermic peak indicates the beginning of a thermo-oxidative reaction. The temperature at the onset of the exothermic peak is noted. A better stabilized sample is characterized by a higher temperature for the onset.

100 parts of Lupranol 2084 (RTM BASF; polyol) are admixed with 0.45 parts of a stabilizer composition, which consists of Irganox 1135 (RTM BASF; 0.32 parts based on 100 parts of polyol), Irganox 5057 (RTM BASF; 0.10 parts based on 100 parts of polyol) and a compound of formula I according to the invention (0.03 parts based on 100 parts of polyol). In comparative example 35a), no stabilizer composition is added.

Lupranol 2084 (RTM BASF) is a trifunctional polyether polyol, which contains predominantly secondary hydroxyl groups and which possess a hydroxyl number 48 mg KOH/g, a water content less than 0.1% and an acid number less than 0.06 mg KOH/g.

Irganox 1135 (RTM BASF) is a phenolic antioxidant and contains 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionic acid iso-octyl ester as depicted:

Irganox 5057 (RTM BASF) is an aminic antioxidant and is a technical mixture obtained by the reaction of diphenylamine with diisobutylene, comprising

-   -   α) diphenylamine;     -   β) 4-tert-butyldiphenylamine;     -   γ) compounds of the group         -   i) 4-tert-octyldiphenylamine,         -   ii) 4,4′-di-tert-butyldiphenylamine,         -   iii) 2,4,4′-tris-tert-butyldiphenylamine,     -   δ) compounds of the group         -   i) 4-tert-butyl-4′-tert-octyldiphenylamine,         -   ii) o,o′, m,m′, or p,p′-di-tert-octyldiphenylamine,         -   iii) 2,4-di-tert-butyl-4′-tert-octyldiphenylamine,     -   ε) compounds of the group         -   i) 4,4′-di-tert-octyldiphenylamine,         -   ii) 2,4-di-tert-octyl-4′-tert-butyldiphenylamine, and             wherein not more than 5% by weight of component α), 8 to 15%             by weight of component β), 24 to 32% by weight of component             γ), 23 to 34% by weight of component δ) and 21 to 34% by             weight of component ε) are present.

TABLE 1 temperature of onset example tested sample [° C.] 35a) ^(a)) 100 parts polyol without 132 stabilizer composition 100 parts polyol with 0.45 parts stabilizer composition containing compound 35b) ^(b)) (201) 188 35c) ^(b)) (202) 193 35d) ^(b)) (205) 193 35e) ^(b)) (206) 197 35f) ^(b)) (207) 194 35g) ^(b)) (214) 194 35h) ^(b)) (215) 195 35i) ^(b)) (216) 193 35j) ^(b)) (218) 191 35k) ^(b)) (219) 192 35l) ^(b)) (220) 192 35m) ^(b)) (222) 191 35n) ^(b)) (223) 189 35o) ^(b)) (224) 190 ^(a)) comparative ^(b)) according to the invention

EXAMPLE 36 Stabilization of Polyether/Polyurethane Soft Foam

Preparation of Polyether/Polyurethane Soft Foam:

0.71 g of a stabilizer composition (0.45 parts based on 100 parts of polyol), which consists of Irganox 1135 (RTM BASF; phenolic antioxidant as described at example 35; 0.32 parts based on 100 parts of polyol), Irganox 5057 (RTM BASF; aminic antioxidant as described at example 35; 0.10 parts based on 100 parts of polyol) and a compound of formula I according to the invention (0.03 parts based on 100 parts of polyol), is dissolved in 157.1 g Lupranol 2084 (RTM BASF; polyol as described in example 35). In case of comparative examples 36a) and 36f), no stabilizer composition is added. 9.84 g of a solution consisting of 1.88 g Tegostab BF 2370 (RTM Evonik Industries; surfactant based on polysiloxane), 0.24 g Tegoamin 33 (RTM Evonik Industries; general purpose catalyst based on triethylene diamine) and 7.7 g of deionized water are added and the reaction mixture is stirred vigorously for 10 seconds at 2600 rpm. 0.31 g Kosmos 29 (RTM Evonik Industries; gelling catalyst based on stannous octoate) is then added and the reaction mixture is again stirred vigorously for 18 seconds at 2600 rpm. 92.19 g of Lupranat T80 (RTM BASF; toluene-2,4- and toluylene-2,6-diisocyanate mixture) is then added with continuous stirring for 5 to 7 seconds at 2600 rpm. The mixture is then poured into a 20×20×20 cm cake-box and an exothermic foaming reaction takes place as indicated by an increase of temperature. The foam blocks are cooled and stored at room temperature for 24 hours.

All prepared foam blocks show a comparable initial white colour.

Anti-scorch Testing

Scorch resistance is determined by static heat aging, i.e. static alu-block test. The foam blocks are cut into thin tubes (2 cm thick, 1.5 cm in diameter). From each foam block, a thin tube is taken as foam sample. The foam sample is heated in an aluminum block.

The temperature is kept at 180° C. for 30 minutes.

The scorch resistance is assessed by measuring the colour of the foam sample after aging. The measured colour is reported in terms of Yellowness Index (YI) determined on the foam sample in accordance with the ASTM 1926-70 Yellowness Test. Low YI values denote little discoloration and high YI values severe discoloration of the samples. The whiter a foam sample remains, the better the foam sample is stabilized.

TABLE 2 Yellowness index after 30 minutes example employed polyol component at 180° C. 36a) ^(a)) 100 parts polyol without 26 stabilizer composition 100 parts polyol with 0.45 parts stabilizer composition containing compound 36b) ^(b)) (201) 1 36c) ^(b)) (222) 2 36d) ^(b)) (223) 1 36e) ^(b)) (224) 3

Footnotes are listed at table 1.

TABLE 3 Yellowness index after 30 minutes example employed polyol component at 180° C. 36f) ^(a)) 100 parts polyol without 25 stabilizer composition 100 parts polyol with 0.45 parts stabilizer composition containing compound 36g) ^(b)) (202) 2 36h) ^(b)) (205) 1 36i) ^(b)) (206) 1 36j) ^(b)) (207) 1 36k) ^(b)) (214) 2 36l) ^(b)) (215) 1 36m) ^(b)) (216) 2 36n) ^(b)) (218) 2 36o) ^(b)) (219) 2 36p) ^(b)) (220) 2

Footnotes are listed at table 1.

EXAMPLE 37 Stabilization of Polypropylene

Method 1:

The employed mini-extruder, which is commercially available from DSM, enables a flow of the melted polymer in a circle, i.e. two screws in a twin-screw arrangement press the melted polymer to the outlet, which is connected to the inlet zone of the extruder. The temperature of the steel barrel of the mini-extruder can be regulated and the inlet zone of the extruder can be purged with a gas, which allows the removal of entrapped air originating from the loading of the polymer sample. Furthermore, a sensor determines the force, which is exerted by the melted polymer onto the barrel during rotation of the two screws. A change in the viscosity of the melted polymer leads to a change of the force.

The steel housing of the extruder is set at a temperature of 280° C. and the inlet zone is set under a nitrogen flow of 20 mL/min. At a screw speed of 50 rpm, 9 g of a mixture, which consists of 8.955 g of a pipe grade polypropylene random copolymer (99.95% of the overall mixture) and 0.0045 g of a compound according to the invention (0.05% of the overall mixture) are loaded. In case of comparative example 37a), a compound according to the invention is not added. Said polypropylene random copolymer itself already contains 0.2% tetrakis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionyloxymethyl]-methane, 0.2% 1,3,5-tri-(2,6-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 0.1% tris-(2,4-di-tert-butylphenyl)phosphite and 0.05% calcium stearate.

Tetrakis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionyloxymethyl]methane is a phenolic antioxidant, which is contained for example in Irganox 1010 (RTM BASF), as depicted:

1,3,5-Tri-(2,6-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene is a phenolic antioxidant, which is contained for example in Irganox 1330 (RTM BASF), as depicted:

Tris-(2,4-di-tert-butylphenyl)phosphite is a phosphite stabilizer, which is contained for example in Irgafos 168 (RTM BASF), as depicted:

After loading, the screw speed is set to 100 rpm and the force exerted on the barrel is recorded. The test is conducted for 10 min under nitrogen at a flow rate of 20 mL/min. After a short period, a steady decrease of the force is recorded. The decrease of the force is quantified as slope of the force-to-time curve, wherein the slope is calculated between the time period of 7 and 10 minutes. The curve is rather linear during said period. The decrease of the force with time is taken as degree of melt-degradation of the polymer sample.

Desired is a minimum of degradation, which is expressed by a small value for the slope of the curve. No degradation would mean zero slope.

The results are shown in table 4.

Method 2: Multiple Pass Extrusion Test

2500 g of polypropylene random copolymer (as described under method 1 including the mentioned additives) is blended with 1.25 g of a compound according to the invention and compounded under nitrogen at 220° C. with a twin screw extruder. In case of comparative example 37t), a compound according to the invention is not added. The pellets are extruded 5 more times at 280° C. under air. The melt flow of the pellets after the 5th extrusion is measured at 230° C. with a weight of 5 kg according to ISO 1133:1997.

A very small change of the melt index indicates less degradation. Ideally, there would be no change in melt flow.

The results are shown in table 5.

TABLE 4 example tested composition method 1 [slope] 37a) ^(a)) without addition of a compound according −0.8 to the invention with compound 37b) ^(b)) (201) −0.2 37c) ^(b)) (202) −0.45 37d) ^(b)) (205) −0.48 37e) ^(b)) (206) −0.54 37f) ^(b)) (207) −0.47 37g) ^(b)) (209) −0.42 37h) ^(b)) (210) −0.38 37i) ^(b)) (211) −0.4 37j) ^(b)) (214) −0.56 37k) ^(b)) (216) −0.4 37l) ^(b)) (218) −0.44 37m) ^(b)) (219) −0.43 37n) ^(b)) (220) −0.31 37o) ^(b)) (221) −0.34 37p) ^(b)) (222) −0.19 37q) ^(b)) (223) −0.14 37r) ^(b)) (224) −0.17 37s) ^(b)) (226) −0.09

Footnotes are listed at table 1.

TABLE 5 method 2 [melt flow (5 kg/230° C.) after example tested composition 5th extrusion] 37t) ^(a)) without addition of a compound according 3.35 to the invention with compound 37u) ^(b)) (201) 2.6 37v) ^(b)) (222) 2.2 37w) ^(b)) (224) 2.6

Footnotes are listed at table 1. 

The invention claimed is:
 1. A composition comprising a) a polyolefin, a polyester polyol, or a polyurethane; b) compound having a structure,

 and c) an additive selected from the group consisting of a phosphite, a phosphonite, an acid scavenger, a phenolic antioxidant, and an aminic antioxidant.
 2. A composition according to claim 1, wherein component b) is contained in an amount of 0.005% to 10% based on the weight of component a).
 3. A composition according to claim 1, wherein the weight ratio of b) to c) is from 4:1 to 1:20.
 4. A composition according to claim 1, wherein additive c) selected from the group consisting of a phosphite, and a phenolic antioxidant.
 5. A process for protection of a polyolefin, a polyester polyol, or a polyurethane susceptible to oxidative, thermal or light-induced degradation comprising incorporating into or applying onto the polyolefin, polyether polyol, or polyurethane a compound having a structure

and an additive selected from the group consisting of a phosphite, a phosphonite, an acid scavenger, a phenolic antioxidant, and an aminic antioxidant. 